South Side
by fallenangel1115
Summary: Destiel AU. Booksmart Castiel is in trouble with the police, again, but they offer him a way out. He can become an informant in a gang where he meets Dean, a street smart troublemaker. Warnings inside.
1. Arrested

**AN: I'm just going to lump the warnings together for the whole story. Drug use/abuse, alcohol use/abuse, strong language, gang activity, violence, mild sexual themes. **

Castiel woke up with a stiff neck and a sore back on a very uncomfortable mattress. He sat up and swung his feet over the edge to place them flat on the floor which made his stomach churn at the movement. His dark brown hair always stuck up at weird angles when he woke up so he raised a hand to smooth it out.

His left hand came up with it.

Castiel groggily opened his eyes and found his hands in handcuffs. _Shit_, he thought as he slowly started to remember why he was in a tiny jail cell.

"Oh good, you're up," Castiel heard someone say. It was the black cop that had helped arrest Castiel last night. He was standing outside of the cell with crossed arms and a smug smile. His name was maybe Henderson or Henricks or something, Castiel couldn't recall. It was hard to remember anything with a pounding headache to accompany his hangover.

Castiel squinted up at the officer. "Can I go yet?"

"Nope. You're going to tell my partner and I what happened last night."

Castiel groaned and closed his eyes again. He could hear the door to his cell being opened and then he was pulled roughly to his feet which did no favors for his uneasy stomach.

The officer, whose name still escaped Castiel, led him to an interrogation room. Castiel sat down before he realized there was another cop already in the room. She was tall with very short brown hair and smiling at Castiel. Her smile was kind, unlike the officer who dragged him in here.

_Was she there last night?_ Castiel couldn't remember.

"Castiel, why don't you tell us what happened last night?" she asked. Castiel read her nametag on her blue uniform as "Mills."

"Officer Mills," Castiel started, rubbing his temples with both hands, "can I have some water, please?" She looked at the cop that brought him into the room and nodded. He left.

"Thanks," Castiel said.

"Not a problem," she answered. She had a file in front of her on the table and opened it. "So, this isn't the first time you've been in trouble, right?"

Castiel just shook his head. The door opened and the other guy was back. Castiel nodded his thanks before chugging the whole cup.

"Now," Officer Mills continued, "Officer Henriksen and I don't think you were the one responsible for last night."

Castiel just raised his eyebrows.

"We think this was your brother's doing but he got away before we could catch him," Henriksen said, sitting next to Mills across from Castiel, who didn't say anything.

"Was he behind the other stuff on your sheet, too?" Henriksen said. "You don't exactly look a stoner or a thief."

"You don't know anything about me," Castiel said icily, meeting Henriksen's eyes with a glare across the table.

"Look, we're trying to help," Mills said, breaking the tension. Castiel shifted his eyes over and eased up on the glare.

"I know, but what can you do? I stole that car last night, I shoplifted and the weed was mine. My brother had nothing to do with it, any of it," Castiel argued.

"I don't think someone who attended such a prestigious high school, college prep school really, wouldn't be so stupid," Henriksen said.

"Key word being 'attended.' It might not be in your little file, but they kicked me out. They didn't want someone who went to juvie for drugs and fighting."

"Fighting? What happened?" Officer Mills asked.

"Someone at school was being a dick," Castiel shrugged. Henriksen and Mills shared a look.

"You know, normally grand theft auto would scare people. It's a considerable amount of jail time. Especially for someone with a record," Henriksen pointed out.

Castiel swallowed and looked down at his handcuffed hands in his lap. He was scared, sure. But that wouldn't help. Being reasonable and figuring something out would help here.

"We know you're smart and you seem like a good guy," Mills said and Castiel scoffed to himself. He wouldn't say the same thing. "We might have a way to help you if you help us."

"How would you like to be an informant?" Henriksen asked. Castiel looked up, confused.

"We're working on getting information on a gang. They're small time, not a lot of guys, and they just sell weed. However, we're trying to being some of them in and we could use you," Mills explained.

"You want me to join and snitch on a gang?" Castiel asked doubtfully. "Doesn't that sound a little dangerous?"

"We'll keep you safe," Mills reassured him. "We just want you to have another option besides jail. You're only twenty and like I said, we want to help."

Castiel considered it for a moment. It wouldn't be fair for him to go to jail because stealing the car was his brother, Gabriel's, idea. He was lying to protect him. Again. Castiel had covered for Gabriel for the shoplifting and the weed was thrown to him because Gabriel couldn't get caught with it again. Family always came first but that didn't mean Castiel needed to go to jail and they still couldn't prove Gabriel had anything to do with last night.

"Fine," Castiel agreed. "What do I have to do?"

* * *

Castiel finally walked through the front door of his apartment after his rough night, and morning, and was really not in the mood to have to deal with Gabriel.

"Castiel, man, where have you been?" Gabriel asked, pulling him into a hug that Castiel reluctantly returned.

"Covering for you. Again," Castiel said as he broke the hug.

"Hey, I'm sorry. I couldn't get caught doing something stupid. You know that I'm on probation," Gabriel stated.

"Yeah, well you're lucky I'm not. Or going to jail," Castiel said as harshly as possible.

Gabriel didn't say anything.

"I'm going to bed. I didn't sleep very well in a jail cell last night," Castiel snapped.

He slammed his bedroom door shut leaving Gabriel standing alone, feeling guilty, in their living room.


	2. Turf War

Not too far from where Castiel woke up in jail and at about the same time, someone else woke up.

Dean blinked awake as his alarm blared before slamming the clock on the bedside table to turn it off. He sat up and turned, throwing his legs over the edge of the bed. Sitting on the edge of the bed, he rubbed sleep out of his eyes while the clock read 8 am in searing red numbers.

He shuffled out of his small bedroom to a slightly bigger living room that had a combined kitchen and eating area across it. The apartment's other bedroom and single bathroom were on Dean's right as he headed towards food and coffee with the front door on his left. He passed the crappy, old plaid sofa and run-down TV as he sighed from being up so early.

The apartment's other occupant was already awake and made coffee for the both of them. _He is way too happy to be awake this early_, Dean thought about his brother, Sam.

"Morning," Sam smiled. Dean just grunted and accepted the cup of black coffee handed to him.

"Why are you up so early?" Dean asked, finally starting to actually wake up. "It's a freaking Saturday, Sam."

"It's late May, finals are coming up," Sam said, like it was obvious.

"And?"

"You are so not a morning person. A bunch of us are getting together to study at the library," Sam explained.

"You and only you would be happy about that," Dean teased, taking a long drink of coffee. "But someone's gotta be the brains of this family and it sure ain't me."

"Would you be able to drop me off before you go to work?"

"Sure," Dean said, "is that one girl going to be there?"

"Who, Jessica?" Dean nodded. "Maybe."

"You're not studying at all, are you?" Dean smirked, finishing his coffee.

"Shut up," Sam said with a laugh. "Can you take me?"

"Yeah, let me get dressed and we can go," Dean got up, put his mug in the sink and headed to his room to change.

Once Sam was at the library to supposedly study, Dean headed to work at Singer Auto where he was a mechanic. Sam and Dean's dad used to own the place with Bobby Singer but he passed away a few years ago.

"Hey, Bobby," Dean greeted as he walked into the shop.

"Ready to get to work?" came the gruff reply. He was in his office, behind his desk, wearing his trademark baseball hat with the garage's logo.

Dean smiled. He was always ready to work on cars, could work for hours and it would fly by.

This particular Saturday wasn't too busy so Bobby let Dean go after five hours at two. He said bye to Bobby, grabbed his leather jacket and headed to his own 1967 Chevy Impala. As much time as he put into the cars at work, he put about ten times more work and love into this car. Besides Sam, this Impala and their crappy apartment was all their dad really left Dean. That, and debt.

Dean drove to where he usually went after work, a parking lot of a convenience store. A group of guys were already sitting on the curb, or standing, in front of the store. The owner tried to get them to stop loitering once but a group of guys with guns aren't easily swayed.

A few of the guys greeted Dean as he got out of his beloved car and he nodded back. He walked over to one guy and shook his hand.

"Hey, Benny," Dean said to a man with an old-fashioned hat and a short-trimmed beard.

"How was work?" Benny answered.

"The usual." To be honest, Benny was the only guy that Dean really liked in this group. The rest were just low-life gang members.

_You're not much better_, Dean thought. The nicer side of his brain chimed in with, "_You joined for the right reasons." _

_"Like that matters," _came the retaliation.

"_Sometimes, that's all that matters."_

Dean's internal moral crisis was interrupted by the gang's leader, wearing all black and who had an air of power about him.

"Good, we're all here," he said, looking pointedly at Dean. "Now we can get to business. It seems as if someone has been selling on our turf."

Dean rolled his eyes while some of the guys started yelling and swearing. It just seemed petty to Dean but some of them appeared to actually be offended which kind of made Dean laugh.

"Something funny, Winchester?" the leader asked.

"No," Dean said, turning his laugh into a cough.

"We know it was, don't we?" he continued. "Why don't we find some of them and make them pay!"

As the cheers turned to excitement, Dean walked over to the black-clad man to talk.

"Are you sure you want to start a war, Crowley?"

"They're the ones who want a war," Crowley argued.

"Someone's going to get hurt."

"You're going to get hurt," Crowley said menacingly, getting in Dean's face, "if you don't do as I say."

Dean wasn't scared of Crowley but he wasn't going to fight him.

"I'm just saying…"

"We can't let those guys sell on our turf, to our people. You know how we work, this is why we're here," Crowley reasoned.

"No, you know why I'm here," Dean snapped. The group had started to pay attention now and had gone quiet. Dean stepped back before it escalated into something no one wanted.

"All right boys," Crowley smiled over Dean's shoulder. "Go kick some ass."

Dean and Benny walked down the street, following Crowley's orders even though neither of them wanted to. They had been walking for so long it had turned dark.

"This is bullshit," Dean spat.

"I know, brother, but it's what we have to do," Benny tried to reason. "It's either we try to find of their guys to beat up or we get beat up for not listening."

Dean didn't say anything and just took a drag from his cigarette.

"Besides," Benny went on, inhaling off his own smoke, "we can't have anyone else selling to our people, our customers. That's how we get paid."

"Speak for yourself, I have a real job," Dean countered.

"So do I, the diner, but extra money never hurt anyone," Benny said. Dean couldn't argue against that and kept smoking. "You should back Crowley up, you are his second in command."

"I never asked to be."

Both of them finished their cigarettes, crushing the butts under their boots.

Right when they continued walking, they heard a gunshot that sounded like it came from the street over. They looked at each other and then started running.


	3. GSW

Dean and Benny followed the sound of the gunshot. They ran down the street, turned right and then turned right again to head up the next street.

The two immediately stopped running when they heard anguished moans coming from an alley on their right. Both of them cautiously walked in to the dark alley, pulling their guns from the waistbands of their jeans. The next thing they saw was not pleasant.

Sitting against the wall of the alley, partially propped up on a dumpster, was one of their own. Jake's breathing was shallow and both of his hands were covering the lower right side of his abdomen.

"Benny, call an ambulance," Dean commanded. He pulled his phone out to do so. "Hey, man, stay with me, you're going to be fine," Dean said to Jake, kneeling next to him. "Just keep pressure on it, okay?"

Benny had hung up despite the dispatcher's pleas to stay on the line. "What happened?" he asked.

"Two of them. Had a gun… one tried, to stop… the other. Shot me…while they wrestled… for it," Jake said weakly, in obvious pain.

"Michael's guys?" Dean asked. Jake nodded.

"Which ones?" Benny wanted to know.

"Zac- Zachariah… and Uriel," Jake said with labored breaths. His eyes started to close.

"Jake!" Dean yelled. "Stay with us, damn it! Where the fuck is the ambulance?" Dean said, looking behind him towards the street. As he said that, distant sirens could be heard.

"Jake, they're almost here, come on, brother. Hold on," Benny pleaded. Jake's eyes were closed but there was still a slight rise and fall of his chest.

Dean and Benny walked out of the alley to direct the paramedics into the alley. The ambulance pulled up and two people in all navy hopped out of the back with a medical bag and a stretcher. Dean just pointed into the alley and they headed in.

"You two called?" the driver asked as he hopped down from the front of the ambulance. Dean and Benny nodded. "Stay here, the cops will want to talk to you."

"You got it," Dean said. The paramedic followed the other two into the alley. As soon as he was gone, Dean and Benny began to walk away. When they heard police sirens, they began to walk faster.

"Let's go to the garage," Dean suggested. Benny nodded.

An hour later, the gang had assembled in Bobby's garage. Bobby didn't approve of the gang, or Dean's involvement, but he knew why he did it so he let them hang out every once in a while.

"All right, what the hell happened tonight?" Crowley demanded to know.

Dean told everyone that Jake had been shot and by who, leading to cries of outrage. They wanted someone to pay.

"Everyone calm down," Crowley snapped. They immediately all shut up. "If we're going to war, we're going smart. You have to figure they'll be expecting a hit tonight, in retaliation, right?"

No one answered.

"So what do we do?" Crowley asked, looking specifically at Dean.

"We wait, let them panic," Dean suggested.

Crowley smiled a truly evil smile. "We wait," he agreed.

Dean finally came home to the apartment he shared with Sam and found him on the couch watching T.V.

"Hey, where've you been?" Sam asked.

"Out," Dean responded. "How was studying, how's Jess? You ask her out yet?"

"Don't change the subject."

"Did you?"

"No," Sam sighed, realizing Dean wasn't giving any other answers to where he had been. "Not yet."

"Aw, come on, Sam!" Dean said, heading to their fridge and grabbing a beer.

"Wanna grab me one?" Sam asked hopefully.

"Dude, no. You're 16," Dean answered with a small laugh.

"You're only twenty!"

"I'm rounding up," Dean smirked as he opened the can. He joined Sam on the couch to watch some late night T.V. Dean found it difficult to get what happened tonight out of his mind and to stop worrying about the upcoming war that was sure to erupt.

"Dean," Sam said cautiously. Dean drank his beer and kept his eyes on the T.V. "I know where you were, or at least who you were with. It's not hard to figure out."

"What's your point?" Dean said, sounding exhausted. They had had this argument many times.

"You know they're bad news, that's my point. I don't want you to get hurt or to get in trouble."

"I don't have a choice, Sam."

"Bullshit, you always have a choice. You taught me that."

"Not this time," Dean snapped, finally turning to look at his brother. "I'm doing this to protect you. And Bobby."

"Really? How?"

Dean sighed and finished his beer. He got up and went to the tiny kitchen, setting the empty can on the counter. He grabbed the last beer from the fridge and rejoined Sam.

"Dean, just talk to me."

Dean didn't answer as he sat back down and opened his beer. The two just watched T.V until they were both too tired and Sam didn't ask Dean anything else.

Castiel sat on a bench along the street trying to be inconspicuous behind a newspaper. Across the street and to his left were the two guys he was supposed to talk to. They were about Castiel's age but seemed older because they were kind of intimidating.

According to Mills and Henriksen, these two were Dean Winchester and Benny Lafitte and regularly sold on this corner. The plan was for Castiel to buy some weed from them, which shouldn't be too hard. Or at least that was what Castiel was telling himself. The two guys had short criminal records, nothing serious.

Castiel got up before he could psych himself out and walked over. _Stick to the plan_, he thought.


	4. Meet and Greet

Dean and Benny were standing on the corner, each smoking a cigarette. Castiel opened his mouth to speak but before he could say anything, Dean interrupted him.

"About time you came over here," Dean said with a smug half smile. "Hiding behind a newspaper? Really?"

Castiel closed his mouth and felt his cheeks get warm as Benny laughed. _Go figure, they're douchebags,_ Castiel thought.

"You cost me ten bucks, I bet Dean here you'd take ten more minutes to come over here," Benny said, still smiling.

"So, you want to buy, right?" Dean asked, crushing his cigarette butt under his boot and accepting the money from their bet from Benny.

"Uh, yeah," Castiel said. It came out weaker than he had hoped.

"See, here's the thing," Dean said, looking right at Castiel. Castiel almost looked away because his gaze was so intense, close to threatening, but he stared right back. "We don't know you. Or anything about you."

"We don't know if we can trust you," Benny clarified. Castiel nodded his understanding.

"Look, we're here most days. You'll just have to come back," Dean shrugged.

"All right," Castiel agreed and began to walk away.

"What a weird, dorky guy," Dean said. He lit another cigarette as he watched Castiel walk away.

* * *

Later that day, Castiel met up with Mills and Henriksen at the same precinct where he spent the night a couple nights ago.

"How'd it go?" Mills asked.

"Not very well," Castiel answered honestly. "They don't know me, so they don't want to sell to me yet."

"So, you have to keep trying," Henriksen said, "get to know them."

"Right," Castiel nodded. It would take some time, but he would easily get to know Dean and Benny, even though they seemed kind of like jerks.

"All right, Castiel, just keep us updated," Mills said before they walked Castiel out of the building.

* * *

Castiel returned to a thankfully empty apartment. He especially didn't want to deal with Gabriel right now. He went to his bedroom, kicked his shoes off and flopped back onto his bed. He just started to relax when he heard the front door open.

"Little brother, you home?" Gabriel called. Castiel groaned.

"I'm younger, not little."

Gabriel appeared in the door to Castiel's bedroom. "You left before me this morning, what were you up to?"

"That's not surprising, you usually sleep late," Castiel argued.

"That's fair," Gabriel agreed. He popped a lollipop into his mouth that came out of nowhere. "You're not in trouble for Friday night, are you?"

"It's fine, Gabriel. I'm not in trouble," Castiel said, rolling onto his stomach.

"Because the shoplifting and weed was on me, too. I don't want to ruin your life more. I know the fight wasn't your fault either, that was because of…"

"Gabriel," Castiel snapped, "I'm fine, everything's fine." He grumbled the last part into his pillow. Castiel really didn't want to go there. Gabriel left and Castiel drifted into a fitful sleep.

* * *

Dean woke up the next weekend at the same time as last Saturday, 8 AM, and headed to work. He got lost in his work, fixing car after car, until Bobby told him it was three and he could go.

After work, he drove to the usual parking lot to meet up with the guys. Immediately, Dean noticed someone who hadn't been around in a week.

"Jake!" Dean exclaimed, getting out of his Impala. He walked over and shook his hand. "Welcome back, man."

"Thanks, Dean. And thanks for being there, calling an ambulance and everything," Jake said.

"Of course. Cops didn't give you too hard of a time I hope?"

"Nothing I couldn't handle," Jake grinned.

"Boys," Crowley said, interrupting the reunion and getting everyone's attention. "Tonight, we're having a party, at my place of course."

Dean rolled his eyes. Crowley thought his house was hot shit but it wasn't anything special. It was just better than what anyone else had.

"Since it seems Michael is gearing up his boys for a good old-fashioned turf war," Crowley paused, "we're going to need numbers. Bring some friends by."

They guys all started talking when Crowley was done. Dean turned to Benny.

"What about the guy who tried to buy from us a week ago and on Wednesday?" Dean asked. The same guy had come back on Wednesday and they told him pretty much the same thing, they didn't know him.

"He's still weird, but what the hell. Let's go to our usual spot and see if he shows."

* * *

Sure enough, there was the guy they hadn't sold to yet on his usual bench. He was already there when Dean and Benny showed up.

Dean and Benny assumed their usual position and waited for him to come over.

"Hey man," Benny greeted. Cas nodded.

"We have a chance for you to get to know us, our whole crew. You feeling like a party tonight?" Dean said.

"Sure," Castiel said, slightly uneasy.

"All right then," Dean said, lighting a cigarette. "What's your name, anyways?"

"Castiel," Castiel said. Dean raised his eyebrows but didn't say anything about the unusualness of the name.

"I'm Dean, this is Benny," Dean said, barely attempting to blow smoke out of Castiel's face.

Castiel coughed a little as Benny told Castiel Crowley's address and time to show up.

"We'll see you later," Dean said and Castiel left.

Benny smiled as he took a drag from his cigarette.

"What?" Dean snapped, inhaling of his own.

"I don't know if that's the kind of guy Crowley was looking for in his little pissing match with Michael, brother."

"Well, we want to bring someone. If he's not cut out then he just gets to come to a party, all right?"

"All right," Benny agreed.

* * *

Castiel got home and found Gabriel making something that smelled delicious in their kitchen. He flopped on the couch and closed his eyes.

_Holy shit,_ Castiel thought, _I got invited to a party by gangbangers._

"Where've you been, little brother?" Gabriel wondered.

"Out," Castiel replied.

"Obviously," Gabriel rolled his eyes. "I meant where. Are you getting into shenanigans? You know how I feel about shenanigans, I want to be taken with."

Castiel just sighed.

"Whatever. What are you doing tonight?" Gabriel asked.

"Going to a party, surprisingly enough."

Gabriel choked on a sample of whatever he made.

"Wha-a what? Se *cough* Seriously?"

"Yes."

"Can I *cough* come?"

"No."

"Why not?"

"I don't think I get a plus-1."

"Maybe I know them."

"Trust me, you don't."

"Come on, Cassie!"

"Gabe, just drop it." And surprisingly, he did.

**AN: Thanks for reading! I'll keep updating pretty regularly.**


	5. Party

Castiel shared a dinner with Gabriel that was only a little tense. The casserole was amazing which didn't surprise Castiel. Gabriel had always been a foodie and could cook like a pro. When Castiel had done the dishes and thanked Gabriel, he headed to his room to call Officer Jody Mills.

"Hello?"

"Officer Mills? It's Castiel Novak."

"Is everything okay?" was her worried response.

"Yeah, I'm fine. Dean and Benny invited me to a party. Should I go?"

"Sure, this is good. You can get close to all of them and get information. Just promise me one thing."

"What's that?"

"Try not to get in trouble? Be careful."

"I'll try. Thanks," Castiel said before hanging up. He felt a pang of sadness at Jody's obvious "mom voice." He started to think about his own mom, the few memories he had of her, but he promised himself he wouldn't do that anymore. He plugged in some earbuds and lost himself in music instead of sadness.

A pounding on his door woke Castiel up. He checked his watch and it read 10 PM. _Shit,_ he thought.

"Don't you have a party to get to?" Gabriel asked through the door.

"Yeah, thanks," Castiel called back.

He got up quickly and started to get ready to leave. He kept his same dark jeans on, his favorite pair, but changed into a plaid button-up with different shades of blue. There was no hope for his bed head so he just left it sticking up everywhere.

Castiel walked into the living room and found Gabriel on the couch in jeans and a simple black shirt.

"You have plans for tonight?" Castiel asked.

"Why yes, I do. Thanks for asking," Gabriel answered.

"Are you going to tell me what they are?"

"Nope. But have fun! Don't do anything I wouldn't do."

"There isn't anything you wouldn't do, Gabriel."

Gabriel's response was his signature eyebrow wiggle. Castiel rolled his eyes and exited the apartment. He walked down the street towards the address he was given with a weird mixture of excitement and fear. This was new territory for him and he didn't know what to expect.

Castiel showed up to a party already in progress. It was warm out so people were scattered on the lawn as well as on the porch and in the house. The house was simple, white and two stories.

He quickly swallowed his fear and walked towards the house. Everyone he passed had either a red Solo cup or a bottle of beer in their hand and seemed to be eyeing him up and down. For the most part, they seemed curious but not malicious.

A guy who seemed to be acting as a bouncer stepped in front of Castiel as reached the front door to the house. He had an evil grin that made him look like he wanted to eat Castiel. It was unsettling. He was also trying to be intimidating except he was about Castiel's height so it wasn't working.

"Can I help you?" the guy sneered.

"I'm, uh," Castiel stammered.

"It's cool," Dean said as he stepped out of the house from behind the asshole. "He's with me." He walked outside and put an arm around Castiel. Dean didn't seem drunk but he smelled like booze.

"Really?" the jerk asked.

"Yes. You don't always have to be such a dick," Dean laughed. "Dick."

Dean kept laughing at his own joke and Dick, Castiel guessed that was his name, glared.

"I've been waiting for ya, Cas," Dean said, guiding him into the house. "Where've ya been?"

"I, uh, fell asleep," Castiel answered, looking around the house and deciding to ignore the nickname Dean gave him who was busy laughing at Castiel's answer. The people all had drinks and stayed focused on their conversations.

The two reached the kitchen and Dean took his arm off of Castiel's shoulders. Benny was standing there with a brunette on his arm who was introduced to Castiel as Andrea. After they had been introduced, Benny and Andrea wandered off.

Dean tried to hand Castiel a cup of the same thing he was drinking.

"Oh, no thanks. I don't really…"

"What, drink? Come on, sure you do!" Dean exclaimed.

Castiel looked down. He didn't really and would prefer not to, especially since the last he did, he got arrested for stealing a car that Gabriel had actually stolen.

"One drink, Cas. No harm in one little drink," Dean teased, pushing the cup into his hand with a smile.

Castiel broke down and took the cup and sipped from it. It was strong, maybe too strong, but it was hard to say no to Dean and his slightly intoxicated goofy smile. And his bright, green eyes… the nickname… Castiel took another drink, a bigger one, to shut his brain up.

Dean kept smiling and threw his arm around Castiel again.

"There's someone you gotta meet, man," Dean said, maneuvering them into the living room. They made it through the crowd of people, both managing to not spill their drinks. The two of them stopped in front of a couch.

On the couch was Crowley with a girl on either side of him. As Castiel recognized Crowley, he also remembered he only knew him from police files he had to pretend to know nothing about. The file probably had his first name but Castiel couldn't remember it.

"Crowley, I brought a guest for you to meet," Dean said, taking Crowley's attention away from the girls. He stood up.

"Crowley. Pleasure. And you are?" he said, extending a hand.

"Castiel," he managed, shaking Crowley's hand. It was a little intimidating to be examined under the dark, searing eyes of a gang leader in all black.

"You seem a little too goody-goody to be hanging around with us," the dark haired girl on the couch said. The blonde girl just smiled. "Like an angel amongst devils."

"Shut up, Meg," Crowley snapped before turning his attention back to Castiel. "Well, it was nice to meet you Castiel. I hope we see you around more," Crowley finished with a bemused smirk.

"Bye, Clarence," Meg said, earning a glare from Crowley.

"Let's go outside," Dean said into Castiel's ear because the song changed and had become ridiculously loud.

On the back deck, there were a lot less people and it was much quieter. The two of them walked to the edge of the deck and leaned on the railing.

"Why'd she call you Clarence?" Dean wondered.

"He's the angel from _It's a Wonderful Life_," Castiel said. Dean just shrugged.

"She must like you," Dean smiled, "she already gave you a nickname."

"Lucky me," Castiel said. He gave it some more thought. "Didn't you give me a nickname, too?"

"Very observant, Cas."


	6. Party, Interrupted

Castiel didn't really know what to say to Dean so he was glad when Dean pulled out his pack of cigarettes from the back pocket of his jeans. It seemed like Dean was flirting but Castiel figured he was seeing something that wasn't there like usual.

"You smoke?" he asked. Castiel shook his head.

He pulled his lighter out of his front pocket and lit one. He took a long drag and turned his head to the left to blow the smoke away from Castiel.

"So, Cas, how did you come to find Benny and me on that street corner? Usually you gotta know somebody."

"Oh, the usual way I guess. Asked around?" Castiel answered, the last word coming out like a question. He knew he sounded like an idiot and he guessed he did because Dean laughed. Castiel turned to his left. Dean wasn't laughing in a mocking way so Castiel laughed too.

They both kept working on their drinks, Dean also on his cigarette, as they stood in a comfortable silence next to each other. Then, there was a commotion that seemed to be coming from the front of the house.

Several people were exiting out of the house, off the deck and towards the gate at the edge of the small yard and into an alley.

Dean set his drink down and put his cigarette out under his boot on the deck. Castiel followed suit with his drink and followed Dean back into the house without either saying anything.

They passed more people leaving the opposite way as they headed towards the source of the problem.

In the front yard there seemed to be a stand-off between Crowley and his guys and another group. Castiel could recognize Crowley's guys from the police files. It was pretty dark and hard to see the other group of guys.

Castiel stayed in the house on Dean's orders as Dean sauntered onto the front lawn to join his gang.

"What do _you_ want, Michael?" Crowley snarled, talking to the guy who looked in charge of what Castiel could only assume was a rival gang. Castiel was trying to see what was going on but stay unseen. This was _not_ part of the deal he made with the police.

"Well, your boys beat up Raphael last weekend. We're here to return the favor," came a cool, snide reply from the rival gang's dark haired leader.

"Your guys shot Jake," Crowley pointed out, crossing his arms over his chest.

"YOU guys were strolling, looking for a fight," Michael said at the same volume but angrier.

"You sold on OUR turf!" Crowley shouted. Crowley's guys were getting angrier as well and started yelling and cursing. A few guys on each side were stepping closer and closer.

Castiel couldn't see which side threw the first punch but it suddenly became an all-out brawl. Crowley got hit with a nice right hook from Michael, Benny was holding his own against a blond guy in a black v-neck and Dean was in a good spot himself. Castiel saw Dean get socked near his left eye but was clearly winning now.

"That all you got, Uriel?" Dean growled, on top of Uriel on the ground. He was really beating him, badly, and Castiel almost went out there to stop him when sirens could be heard not to far away.

Without saying a word, every guy on the lawn bolted in a different direction. Dean looked back at the house, saw Castiel and ran towards him.

"Come on, Cas. We gotta go," Dean said. The two ran through the house, down the back deck's stairs and out the back gate.

They took off together down the alley and almost made it to the main street when a cop care blocked their way. The blue and red lights were nearly blinding. Castiel barely saw Dean, who was right next to him, but he saw him throw something to his left by the dumpsters.

A cop yelled, "Freeze!" A hand grabbed Castiel's and pulled him in the opposite direction down the alley, away from the cops. Castiel blinked away the spots in his eyes and he, of course, was following Dean.

"I bet you're glad I invited you, huh?" Dean smiled.

Castiel smiled back. He wouldn't change this for anything, it was more fun than he'd had in long time which was telling of how boring things had gotten for him.

That smile faded when another cop car blocked them from going down the alley. They turned around again but the cops from the first car had caught up to them on foot.

"Hands in the air!" one of them yelled.

Dean let go of Castiel's hand to put his hands in the air with a smirk. Castiel put his own hands in the air without the same arrogance.

_Not again_, Castiel couldn't help but think.

In the police station, Castiel once again found himself in an interrogation room across from Mills and Henriksen.

"This isn't exactly what we had in mind when we said to infiltrate the gang, Novak," Henriksen started.

"What happened, Castiel?" Mills asked in her usual nice, "mom" voice. Castiel couldn't help but think that these two had mastered the "good cop/bad cop" routine.

"Crowley's party was interrupted by a rival gang. The leader's name was Michael." Henriksen and Mills exchanged a look. Castiel leaned forwards in his chair. "Did you two know about the rival gang?" Castiel accused.

"Yes," Henriksen admitted.

"Don't you think that would be important for me to know? That makes it a lot more dangerous if thugs want to kill me because of who I'm _pretending_ to socialize with!" Castiel snapped, not even trying to hide his anger.

Neither cop said anything. Castiel leaned back in his chair.

"Am I being charged with anything?" he asked.

"No," Mills said.

"Fine, I'd like to leave then," Castiel said, standing up, "call me when you have a better plan."

He left the interrogation room leaving a stunned and silent Mills and Henriksen.


	7. Drive

In the lobby of the police station, Dean was sitting in a chair and holding an ice pack to his left eye. He lowered it and smiled when he saw Castiel.

"Holy crap, Dean. That's a hell of a shiner," Castiel said. It was already nasty, yellow and swollen.

"Thanks, Cas. You should see the other guy," Dean winked with his good eye and put the ice pack back on the other one.

"I did," Castiel said, sitting next to him, "You beat the shit out of him."

"Fuck yeah I did," Dean grinned. "Uriel's a dick."

"Are you free to go?" Castiel asked, which was the best way he could phrase, "Why are you still chilling at a police station?"

"Yeah, I'm waiting for Sammy, my brother, to come get me. Kid just got his license but he's a good driver."

Castiel smiled. He could already tell Dean was proud of his little brother and loved him a lot.

"Do you want a lift home or whatever?" Dean asked, scratching the back of his neck.

"No, that's okay. I can walk."

"Come on, I insist. I invited you to the stupid party and then you got arrested, I feel bad."

"Good point. All right."

Dean left the ice pack on the chair on his other side and the two headed outside to wait for Sam.

As Dean was pulling out a cigarette, he told Castiel, "You should hang around with us more, you know how to have a good time."

Castiel had to laugh. "I didn't do much but I actually had a good time."

"Actually?" Dean said with mock hurt.

"Well, it's not usually a good thing when the cops show up."

"I have to agree with you there," Dean said as he smoked.

The stood quietly for a couple minutes until Dean pointed up the street.

"There's Sam," Dean said, crushing the rest of his cigarette under his boot, "come on."

Sam parked across the street and Dean and Castiel crossed the street. It was tricky because it was busy even though it was close to one in the morning. The car was old but in great condition. It was long, sleek and black. That's all Castiel could tell because he didn't know much about cars.

"Hiya, Sammy," Dean said, getting in and closing the passenger door, "this is Cas. He needs a lift."

"Nice to meet you, Cas. I'm Sam, not Sammy," Sam said as Castiel got into the car behind him, making him laugh.

"Oh, crap. Sam, I lost something," Dean said as Sam pulled onto the street.

"Your fighting skills?" Sam asked, pointing at Dean's black eye.

"No, smart ass. I totally destroyed the other guy, ask Cas."

Sam looked in the rearview mirror at Cas who shrugged.

"He 'totally destroyed the other guy,'" Castiel agreed.

"Are you mocking me?" Dean accused. Both Sam and Castiel had to laugh.

"Well, I'm glad you two are getting along, but do you have to gang up on me?" Dean grumbled, making the other two laugh even louder.

"Did you actually lose something, Dean?" Sam asked seriously when he stopped laughing.

"Yes. Make a right on the next block," Dean said, grateful the teasing had stopped, at least for now.

Dean directed Sam back to Crowley's house.

"Why are we back here?" Castiel asked.

"Just wait here, okay?" Dean said as Sam parked in front of the house. "Two seconds, promise."

"Is he usually that vague?" Castiel asked Sam when Dean was out of earshot.

"No," Sam smiled, "usually it's worse."

Castiel looked out the opposite side of the car from where he was sitting at Crowley's yard. It was still littered with red cups and beer bottles from the party.

"So, Cas, how do you know Dean?" Sam asked as they waited for Dean to get back.

"I, uh… we just," Castiel sputtered. It was hard to explain to Sam, who still seemed like an innocent kid, that he had tried to buy weed from Dean and was trying to get in the same gang. Castiel didn't know how much Sam knew.

"All right, I got it," Dean said, appearing next to the car, making Castiel jump. He didn't see him sneak up.

Dean's hand covered the back waistband of his jeans as he climbed into the Impala. Castiel could only assume it was a gun and he had thrown it in the alley when they ran from the cops.

"All right, we can go," Dean stated.

"What did you lose, Dean?" Sam asked.

"Nothing, just drive."

"No, not until you tell me."

"Sam, can we do this later?" Dean said, shooting a glance back at Castiel.

Sam sighed but must have decided Dean was right and drove away from Crowley's. It was awkward only for a moment until the radio station they had on came back from commercial.

"Journey? Really?" Sam laughed. His hand went to switch the channel but Dean slapped his hand away.

"How do you not like Journey, who are you?" Dean joked.

"I'm driving, I pick the music. That's _your _rule! So shut your cakehole."

"Not if your taste is crap. And she's still my baby, even if you're driving. What do you think, Cas, does Sam get to change it?"

"Oh, I don't know if I want to get in the middle of this," Cas said to stay neutral. Sam and Dean both laughed and left "Faithfully" on.

"Right, so where do you live, Cas?" Sam asked. Castiel gave him directions and they were there in a few minutes. They stopped out front of Castiel's apartment building.

"You kind of live close, we're only a few blocks away," Sam pointed out.

"Thanks for the ride," Castiel said. Sam nodded.

"I'm sure I'll see you soon, Cas," Dean said, turning in the front seat to wink at Castiel.

"Yeah," Cas said, "See ya." Castiel quickly got out of the car before either Winchester could see the blush he could feel.

He went upstairs to an empty apartment. He didn't know where Gabriel was and he didn't care. He collapsed on his bed and closed his eyes, able to replay the wink enough times to fall asleep with a smile on his face.

**AN: Thanks for reading, reviews mean a lot.**


	8. The Usual and Something New

The following Wednesday, Dean and Benny were standing on their usual corner conducting business as usual. They were both smoking and Dean kept looking over at Castiel's bench. He thought he was being more subtle than he was.

"You missing your weird little friend, brother?" Benny grinned.

"What? No," Dean said defensively. "And he's not weird."

"You called him that first," Benny said. Truth was, Dean hadn't seen Castiel since Saturday and he _was_ a little worried. But there was no way he was telling Benny that. He also didn't have any way to contact Castiel.

"Shut up," Dean said because Benny was still grinning. Benny laughed as he took a drag of his cigarette. Dean did the same.

They had relaxed for about a minute before a cop car pulled up and stopped right in front of them.

"Good afternoon, gentlemen," the officer said across the car through the open passenger window. It was Officer Victor Henriksen, a regular thorn in the sides of Dean and Benny, plus the rest of their crew.

"Henriksen," Dean said as a greeting.

"What are you two doing just standing around on such a beautiful day?"

"We're enjoying it," Benny smirked, "sir."

"Just standing around isn't a crime," Dean tried, puffing on his cigarette.

"Actually, it is. It's called loitering."

"Touche," Dean laughed.

"You should know, I've picked you up for it before," Henriksen said.

"Yeah, and nothing stuck because it was bullshit every time," Dean responded, crushing his cigarette boot under his boot.

"Now," Henriksen said, still from the car, "you boys aren't doing anything worse than loitering, are you?"

"No, sir," Benny said, voice dripping with over the top and fake kindness. He dropped his own cigarette butt on the ground and smashed it under his boot.

"Well, now you're both littering," Henriksen said, as he started to get out of his squad car.

"I think we've been here long enough," Benny said quietly with a sideways glance at Dean.

"Usual?" Dean muttered and Benny nodded.

"What are you two muttering about?" Henriksen said, clearly not in a joking mood.

At that, Dean and Benny both took off running down the sidewalk in opposite directions.

Dean, without turning around, could hear pounding footsteps and knew Henriksen was following him.

"Shit," he breathed as he ran. He turned down an alley and sprinted towards the end where he was met with a wooden fence. Dean quickly climbed up a dumpster and jumped, grabbing the top of the fence and dangled there.

"Get back here, Winchester!" Henriksen shouted as Dean hung, his echoing footsteps getting louder and louder.

Dean pulled himself over the fence as Henriksen got there and jumped, narrowly missing grabbing onto Dean's foot.

"Sorry, Vicky, you gotta be quicker than that!" Dean yelled victoriously from the other side of the fence.

"I will catch you, Winchester, just you wait!"

"Oh, I'd love to see that!"

Henriksen could hear Dean's smug laughter as he ran away.

* * *

The next night, Cas was trying to watch T.V. and relax but Gabriel wouldn't shut up.

"I just don't understand this show," Gabriel complained. "What's going on?"

"I don't know, you won't shut up," Cas snapped.

"Whoa, what's with the stick up your ass?" Gabriel responded.

Castiel turned to glare at his brother.

"Just saying," Gabriel muttered, putting his hands up in surrender.

Cas didn't mean to snap at Gabriel, the show really didn't make sense whether Gabriel talked or not, but he had been on edge since Saturday. Henriksen and Mills had failed to mention the rivalry of the gang he was trying to join and the other one. Cas had no idea how dangerous the other guys were and he had the feeling that Mills and Henriksen didn't know either.

"I'm going out," Cas said as he got up off the couch.

"Where?" Gabriel asked.

"Just for a walk," Castiel answered. He usually went for walks when the apartment got too stuffy or he just needed to clear his head.

"All right," Gabriel said hesitantly, "be careful."

* * *

Castiel was walking down the street kicking a rock. He hoped he hadn't gone too far, the streets had kind of all blurred together.

"Cas?"

Castiel's head turned. To his left, Dean was leaning against the wall of a building, smoking.

"Hello, Dean," Castiel said, startled to see Dean.

"What are you doing here, man?" Dean asked with a smile, blowing smoke out of the side of his mouth.

"I was just walking," Castiel admitted, "I don't even know where I am."

"You're at the Roadhouse. Best damn bar in Chicago," Dean paused, "At least that I've been to anyways."

"Are you 21?" Castiel asked, tilting his head. He knew from Dean's police file he wasn't but he had to ask because Cas shouldn't know how old he was.

"No, only twenty. But I round up," Dean winked, "and I know the owner, family friend. You should come in!"

"I'm only twenty, maybe you know the owner but I don't," Castiel protested.

"Well, you know me," Dean smiled. "All the guys are here, if you didn't meet them at Crowley's, you can now."

"I don't know…"

"Come on, Cas. There's plenty of hot chicks in there," Dean stopped, eyeing Castiel for a moment, causing him to shift his weight from foot to foot. "Or guys if that's what you want."

"Not that it's any of your business," Cas said, taking a normally brazen Dean aback, "but I'm not particular."

"Huh," Dean answered, "neither am I." Now it was Cas's turn to be taken aback. He would not have guessed someone like Dean swung both ways.

Dean crushed the butt of his cigarette under his boot and opened the door to the bar, letting music, clinking glasses and laughter filter out into the night.

"Shall we?"

Castiel nodded and followed Dean into the bar.


	9. What Happens At the Roadhouse

As the two of them walked into the bar, Dean was explaining how he knew the owner, Ellen Harvelle, and her daughter Jo.

"I've known them for forever. Ellen's married to Bobby, who's like an uncle to me and Sam," Dean said. He put his brown leather jacket on the back of his chair as they sat at a small wooden table with surprisingly comfortable chairs. The bar was dimly lit but big and spacious. "Bobby used to work with our dad and they all live in the same building as us."

"Used to?" Cas asked. Dean didn't answer, just looked behind Cas, and he just figured he didn't hear him over the music and other noise. The file Cas saw from the police only said that Dean was Sam's legal guardian but not why.

"Winchester, I see you brought your friend around again," a voice drawled behind Castiel. Crowley had walked up to their table.

"Yeah. Cas, you remember Crowley."

"Of course. Great party last weekend," Castiel managed, trying not to sound lame.

"Until Michael and his crew showed up," Crowley paused, lost in thought for a moment. "Glad to see you again, Cas."

"He's a little…uh," Castiel said as Crowley walked away.

Dean just laughed.

"That pretty much describes him."

Quickly, Crowley's spot next to the table was taken by Benny, who actually sat down.

"Evening, gents," Benny said with his slight Southern twang.

"Hey Benny," Dean smiled. Castiel nodded his greeting.

"What are you boys up to tonight?" Benny asked.

"The usual," Dean smirked.

"Drinking, hustling pool and looking for hook-ups?"

"You know me, what else?"

"Can I get you guys anything?" asked a blonde girl who stood next to their table. She said guys but was only focused on Dean.

"Yes you can, Jo," Dean winked. "How about a round of shots?"

"Be right back," Jo said, looking down with a smile.

"You should leave her alone, Dean. She's all over you and you don't feel the same way," Benny said.

"Oh, but it's so much fun," Dean said with a small smile leaning back in his chair.

"That's pretty shitty," Cas chimed in, earning a glare from Dean and a nod from Benny.

"Here you go," Jo said as she set a tray with three shot glasses on their table.

"Thanks, Jo," Dean smiled at her as he grabbed a shot glass as did Benny.

Jo walked away and Dean and Benny looked at Cas expectantly, who still hadn't picked up the remaining shot glass.

"Come on, Cas, take a shot with us," Dean goaded.

"I'd rather not," Cas replied.

There was a brief pause before Dean just shrugged and took the third glass for himself.

"More for me," Dean said, "cheers!" He tapped one of his glasses with Benny's and they threw them back. Dean did the same with his second shot. Cas assumed Dean had been drinking before Cas even showed up but he seemed fine and Cas wasn't going to baby him.

"All right, I'm gonna get a beer and play some pool," Dean said, getting up and heading to the counter Jo was behind. She smiled as he walked over. On the right side of the bar was a group of about five mean looking guys playing pool.

"He's going to mess with those guys?" Cas asked Benny.

"Don't underestimate him, he can handle it," Benny laughed.

"So, this is what you guys usually do?"

"Generally, yeah. This or drag racing behind a store we normally hang outside of."

"Drag racing?" This was news to Castiel who figured Henriksen and Mills didn't know about it.

"The other gang that crashed the party? We race them."

"How do you guys do?"

"Pretty good," Benny laughed, "especially if Dean is racing."

"In his old Impala?" Cas asked doubtfully.

"Whoa, don't let him hear you talk about his baby that way. He's the best we got."

Castiel had to laugh. He watched Dean, who had gotten his beer and had stopped flirting with Jo, and was headed to the pool table. As Benny and Cas sat there, Benny introduced Castiel to some of their usual crew. He officially met Dick, the bouncer from the party, his close friend Edgar and Jake. There were other guys but Cas had forgot their names.

"Well, my girlfriend's here. I'll catch you later, Cas."

Benny got up and headed to the door where Andrea had just walked in. Since Castiel was left alone at the table, he decided to take the tray with the empty shot glasses back up to the bar that Jo was behind.

"Thanks," Jo said, looking shocked. "Most people in here aren't very helpful. Just sloppy drunks. I'm Jo by the way."

"Cas," Castiel said, choosing to stick with the nickname Dean gave him.

"Can I get you something to drink, Cas?" Jo asked.

"No thanks. I'm not much of a drinker," Cas said, taking a seat on a stool across from Jo.

"I'm only 19 so my mom doesn't let me drink here. It's her place."

"Ellen, right?"

"Yeah, how'd you know?"

"Dean told me."

"That would explain it," Jo huffed.

"He said he's known you for a long time."

"Pretty much as long as I can remember, yeah."

"So you know Sam, too?"

"Of course. There's not much I don't know about Dean," Jo sighed. She looked at Dean, who was laughing as he played pool, before she kept cleaning glasses.

"So, you know he…"

"Sells pot?" Cas nodded. "Yeah, I buy from him. Don't tell my mom," Jo said, casting a worried glance behind her that read "Office."

"Why? You don't want to get in trouble or you don't want Dean to?"

"What do you mean?" Jo glared. Cas threw his hands up in the air defensively. He only just met Jo but he could he wouldn't want to get on her bad side.

She gave up glaring and sighed.

"That obvious?" Jo asked, discouraged. She had stopped washing the glasses.

"Yes. And you only had to come to our table once."

"Oh God, you're not a jealous boyfriend are you?"

"What? No, we're, uh, friends." It was weird to use that word describing himself and Dean. They hadn't known each other long and it was kind of a weird situation.

Jo let out a breath of relief.

"Don't worry about me, I don't see Dean like that," Cas assured her.

"I can't help it, you know? He kind of rocks the bad boy thing."

Cas shrugged as Dean walked over to the bar with a wad of cash in his hand and a smirk on his face.

Cas wasn't going to say it out loud but Jo might have had a point.

**AN: Thanks for reading/reviewing/favoritng/following! I appreciate it!**


	10. Stays at the Roadhouse

Dean walked up to Cas at the bar, stood next to him, but turned to talk to Jo across the counter.

"Hey Jo, I have enough to cover last night's drinks, the ones I've had so far tonight and I'd like a couple more shots," Dean smirked. Cas could already see the alcohol was getting to Dean, at least a little, because his cheeks had gotten slightly pink. He could see that even in the dimly lit bar.

He handed some of the money to Jo and put the rest in the back pocket of his jeans. Jo poured two shots of whiskey and pushed them in front of Dean.

"Sure you don't want to drink, Cas? My treat. Those guys sucked at pool."

"I'm all right, thank you. Dean, those guys seem angry."

"Course they are. I just won all their money!" Dean exclaimed, taking one of the shots.

"No, like really mad. Want to kill you mad," Cas said, looking uneasily at the scary guys still by the pool table.

"I can beat them in pool and I can beat them in a fight," Dean said arrogantly, taking the other shot.

"Thanks, Jo," Dean winked.

The door behind Jo labeled "Office" opened and a brunette woman walked out. She had a stern but motherly look about her, with brown eyes and a mouth set in a tight line.

"Jo, take care of the newcomers," she said. Jo went to the table of four young women that had just come in to take their order.

"Hi, Ellen," Dean said with a small smile. Cas noticed Dean stood up straighter when talking to Ellen with obvious respect.

"Don't you 'Hi, Ellen' me, Dean Winchester. You better…"

"I paid, I paid! Ask Jo!" Jo came back to the counter and Ellen did just that. Jo confirmed that Dean had paid off his tab.

"See?" Dean joked.

"Good," Ellen responded, "otherwise I would have kicked you out on your ass."

Dean pulled out money to buy another beer. Ellen got it for him.

"And if any cops ask?" Ellen asked, before handing the beer over.

"I don't know you or your bar. Come on, Ellen. You know I don't talk to cops." Ellen turned to talk to Jo so Dean turned to Cas.

"Let's play pool."

"Are you going to take my money?"

"Why, Cas, I'm offended," Dean said, feigning offense. Cas just raised his eyebrows.

"I'd only take your money if we made a bet, win it fair and square," Dean said, rolling his eyes.

"All right, well I'm not very good, so let's keep money out of this," Cas said.

They played for a while and Dean kicked Cas's ass at it. After the second game, Dean went to the bar to get more drinks. Once he finished flirting with one of the girls from the table of four, he came back for a third game.

During this game, Cas was doing a little better. He had gotten the hang of it a little and Dean was getting a little more drunk as time passed. Benny walked over to the pool table.

"Hey, man. What happened to Andrea?" Dean asked with a slight slur to his words. Cas had been trying to keep track of how much Dean had to drink but it had become impossible.

"We had an argument," Benny said glumly.

"Again? I'm sorry," Dean said. Cas got a hint of boredom in his response and guessed that Benny and Andrea argued a lot.

The girl Dean had been flirting with walked over towards the pool table, eyes focused on Dean. Cas turned around and didn't see her friends in the bar anymore.

She headed straight to Dean and whispered something in his ear. He took her hand and led her towards the back of the bar without a backwards glance.

"Is he… are they…" Cas stammered in disbelief.

"Yup," Benny said, casually picking up the pool stick Dean was using and sinking the nine ball.

"In the bathroom of a bar?"

"Yup."

"I'm guessing this isn't the first time?"

"Far from it."

Cas glanced at the bar. Jo was cleaning, trying to keep busy, but was glaring at the glasses like she wanted to throw them all on the floor. Or at Dean.

Cas and Benny played some pool and it was a much more even match.

The bar had started to clear out when Dean finally came back. Cas looked at his watch which read about two in the morning. The girl Dean was with probably snuck out the back which was probably for the best because Jo probably would have killed her.

Dean stumbled over to the bar.

"Hey, Jo," he grinned, "how about another beer?" He reached into his back pocket but didn't find any money.

"How about you get the hell out before my mom sees you like this and kicks you out forever?"

"Ah, come on, Jo."

Cas and Benny watched the train wreck that was Dean trying to sweet talk Jo into another beer but she wasn't having any of it. Finally, Cas decided to step in.

"I'll get him out of here," Cas said to Jo. He turned. "You're going home, Dean."

He put a hand on Dean's shoulder to lead him towards the door.

"Thank you," Jo said. Cas nodded.

"You need help?" Benny wondered.

"Uh, do you know where his car is?" Cas asked. Benny nodded.

"We'll take him to it and I can drive. I'm used to taking care of my brother when he's smashed," Cas continued.

"I'm not smashed," Dean protested. Cas rolled his eyes.

"Shut up and give me your keys," Cas demanded.

Dean stuffed a hand into his front pocket and handed Cas the keys to the Impala as he steered them towards the door.

"Wow, he really must be drunk to let you drive his baby," Benny laughed.

The three guys walked out the front door. Benny pointed out where Dean's car was, made sure Cas could handle the situation and said goodbye, walking away down the street.

As they got to the Impala, Dean immediately got into the driver's seat. Luckily, it was an older car with a bench front seat.

"Dean, slide over. You're not driving," Cas commanded. Dean silently slid over. Cas carefully climbed in and shut the door. He let out a deep breath before starting the car.


	11. Shameless

"Okay," Cas said quietly. He had just started the Impala and was terrified of hurting Dean's baby. He couldn't piss Dean off, he needed to get into the gang.

As he pulled out onto the thankfully empty street, something dawned on Cas.

"Dean, where do you live?"

"Oh, we're going to my place?"

"Yes. You're drunk and you need to go home and sleep."

"That's it?" Dean said suggestively.

"Yes," Cas said, shifting a little on the seat. He felt Dean move about an inch closer.

"Where do you live?" Cas repeated, trying to ignore how close Dean had gotten. It was difficult.

Dean alternated between giving directions and saying things about Cas coming home with him that were making him blush. His pink lips, his ass, his tousled hair he wanted to make messier…

"Stop, Dean," Cas said. His cheeks were burning and he kept squirming.

"Aw, why, Cas? You embarrassed or some-fin…"

"You can't even talk and we've been driving in circles. Do you have any idea where we are?"

Dean shook his head but was smiling. Cas rolled his eyes. This was ridiculous.

"Give me your phone," Cas insisted. Dean listened. Cas scrolled through the contacts as they sat at a red light and stopped at the one labeled "Sam." He dialed as the light turned green and he eased the Impala into the intersection, still being extremely careful.

"Dean…" a sleepy voice answered.

"Actually, it's Cas."

"Cas? Is Dean okay?" Sam said, suddenly awake.

"Yeah, he's fine. Well, drunk, but he's fine…"

"You think I'm fine," Dean laughed to himself, trying to lean on Cas who pushed him off.

"Hush," Cas said before talking to Sam again. "He doesn't know where he lives right now."

Sam sighed and directed Cas to their apartment when he told him where they were. Cas got them there, parked right out front and hung up with Sam.

"Dean, we're here. Hold on," Cas said, walking around the car to help Dean out of the car.

"So, Cas, you're coming upstairs, right?" Dean mumbled. Cas barely heard him.

"Well, yeah…" Cas answered, guiding Dean up the front steps of his apartment building.

"And then you're staying the night?" Dean asked. The two made it through the front door and Cas pressed the button for Sam to buzz them in.

"No, I'm going to hand you over to your brother."

"You should stay."

"What? Why?" Cas asked, half dragging Dean through the second door and towards the elevator. He pressed the "up" button and waited.

"'Cause you're cute, that's why," Dean said, completely out of it and looking at the floor.

"Come on," Cas said, pulling Dean onto the elevator and pressing 3. He was glad he remembered to ask Sam what floor they were on. He also chose to ignore Dean's comment, like he was ignoring the other ones. Or trying to, anyways. Cas dismissed it as a drunk guy who was used to sleeping with anyone he wanted and that the charm wasn't working.

"I'm serious," Dean slurred.

"Right," Cas rolled his eyes, "you just want to get in everyone's pants."

"Maybe just yours."

Cas felt his cheeks redden, again, as the elevator dinged for the third floor. As he pulled Dean towards apartment 3C on their left, he had to ask himself, _How can he still smooth talk when he's this drunk?_

_He's drunk, he doesn't know what he's saying… or mean it,_ Cas thought, trying to convince himself the flirting wasn't working. _He just want an easy lay, like he's used to…_

Sam must have heard them coming and opened the door to their apartment. Dean looked up and saw his brother.

"SAMMY!" he yelled. Cas immediately clamped a hand over Dean's mouth and Sam helped drag Dean into the apartment.

"Jeez, Dean, you're a mess," Sam scolded.

"Sam, this is Cas," Dean said, "he's staying the night."

"No, I'm not," Castiel insisted, then turned to Sam, "he keeps saying I am."

"Wouldn't be the first time he brought some girl or guy home," Sam sighed.

"I mean, not that there's anything wrong with that," Sam added, seeing Cas's raised eyebrows, "he just usually wakes me up is all. All right, Dean. Bed time."

Sam started to lead Dean towards a bedroom to the right of the front door.

"Make Cas stay," Dean demanded.

"No, Dean, I have to go home," Cas repeated.

"Saaaaam," Dean whined. He began to fight Sam and tried to get out of his grip. The two wrestled for a couple minutes.

"You could stay, we have the couch," Sam suggested, giving up.

"I couldn't, really, it's fine, I can walk home," Cas tried.

"Please," Sam pleaded, "if it will shut him up?"

"All right," Cas gave in, "Dean, I'm staying, on the couch. Now go with your brother."

Dean listened and went with Sam into his room. Cas sighed and kicked off his shoes before sitting on the couch. He leaned forward and started to rub his temples. A clock above the TV read quarter to three in the morning.

Sam must have gotten Dean to go to sleep and walked out of the room, shutting the door behind him.

"I'm sorry about that," Sam said bashfully, "thanks for getting him home. And staying."

"You're welcome, Sam."

Sam grabbed an extra blanket from a closet to hand to Cas before saying goodnight and disappearing into the bedroom behind the couch. Castiel put the Impala's keys and his cell phone on the table in front of the couch and turned off the lamp behind his head.

He lay down and got comfortable but it took longer than he hoped to fall asleep. Cas couldn't help but think about Dean's flirting and how close he was to him right now and that he was staying in his apartment…

_No, _Cas told himself_, that's not happening. Forget it._

He did his best to turn his brain off and go to sleep.

**AN: Thanks for reading! Sorry this chapter's a little short but I'll update again fairly quickly. **

**For the anon reviewer, the relationship will move along, just not yet! Soon, though :)**


	12. Morning After

Cas woke up when the door behind the arm of the couch opened. He propped himself up on his elbow and saw Dean standing in the door way of his room.

Dean was rubbing sleep out of his eyes when he saw Cas on the couch and paused. He was still wearing his clothes from last night, a black T-shirt and jeans. His leather jacket must have been in his room somewhere.

"Ugh," Dean groaned, "it wasn't just a bad dream. Morning, Cas."

"Hello, Dean," Cas said, sitting up on the couch.

"I…" Dean started to say. His hand flew up to cover his mouth and he ran to the bathroom. Cas could hear him throw up violently.

Cas was about to go check on him when Sam opened his bedroom door that was next to the bathroom, both behind the back of the couch, and shuffled out. Sam's hair that was at about his ears was messy and he wore a big gray T-shirt and red plaid pajama pants. He appeared to be moving on auto-pilot and Cas wondered how many times this had happened.

After an awkward few minutes for Cas, Sam walked out of the bathroom, said hello to Cas and headed to the kitchen. It was small and on the opposite side of the couch than Dean's bedroom. As Cas could smell bacon beginning to cook he could also hear Dean brushing his teeth.

Cas checked his phone and saw that it died but the clock above the TV read seven in the morning. Since it was Friday, he could only guess that Sam had school.

When Dean finished in the bathroom, he and Cas waited at the tiny kitchen table for Sam to finish cooking. Cas saw he was making eggs as well.

"Cas, I…uh," Dean began, rubbing the back of his neck, "I didn't do anything embarrassing last night, did I?"

Castiel thought of the girl he disappeared with and the shameless flirting he did with Jo and then him.

"No," Cas lied. Sam placed the food down on the table along with orange juice.

"Eat up," he ordered Dean as he sat down.

"I hate you," Dean mumbled.

"You're welcome," Sam said, munching on bacon.

"I should go," Cas said, not wanting to intrude any more. Dean started to protest, saying he should stay and eat as thanks for taking care of him but Cas said his brother would be worried.

"All right," Dean gave in, "do you want a ride?"

As he said that, his eyes got huge and he dropped his forkful of eggs.

"My car!"

"Dean, it's fine," Cas reassured him, "I drove us here last night."

"You drove my car?" Dean said. Cas wasn't sure if he was mad or not, it was hard to read his expression.

"Yeah," Cas said slowly. He saw Sam had wide eyes and his glass of orange juice paused halfway to his lips.

Dean nodded and continued to eat his eggs.

"I guess that's good. I was clearly in no shape to drive yesterday," Dean said with a mouthful of eggs, "She made it home okay?"

"Yes, not a scratch. I parked right out front," Cas smiled, relieved. Dean smiled back and Sam let out a sigh of relief.

"I really should go," Cas said reluctantly. He hadn't even eaten anything. He stood and headed to the front door. Dean got up to follow him.

"Hey, Benny and I had to move. Trouble with the cops," Dean said quietly, casting a wary glance at Sam. "Let me get your number and I can text you our new spot."

Cas managed to give Dean his number without turning red or stumbling, which he was thankful for.

_Why that would be a big deal, it's not, it's just your number…_ Cas mentally kicked himself.

"I'll text you after I go back to sleep for a while," Dean smiled. Cas smiled back. From the table, Sam coughed.

"I have to, uh, get ready for school," Sam said, heading back into his room.

"Well, I'll see you later then," Dean said.

"Bye, Dean," Cas said, heading down the hallway. Dean shut the door behind him then sat on the couch, picking up his keys.

"Son of a bitch drove my car," Dean laughed to himself. Normally, he'd be furious if someone other than him or Sam drove the Impala. Hell, he barely let Sam drive it.

But something about Cas…

Sam opened his bedroom door, interrupting Dean thinking about Castiel and his car.

"Dean," Sam started.

"Not now, Sam," Dean said, getting up off the couch to head to his room for much needed sleep. He didn't want to deal with Sam to add to his already terrible headache.

"I was just saying, it's not like you to forget stuff when you drink. I'm worried," Sam said. They were on opposite sides of the couch now.

"I remember everything," Dean said with an air of finality that Sam ignored.

"What? Then why did you pretend you didn't?" Sam asked, confusion obvious with his furrowed brow.

Dean sighed and turned to go into his room.

"Dean, come on. Don't do that."

"Do what?"

"Walk away. Just talk to me, man."

Dean looked at the pleading look on his younger brother's face and had to give in.

"Fine," Dean said, sitting on the couch. Sam joined him.

"Why'd you lie?" Sam asked bluntly.

"I said some embarrassing stuff to Cas so I was pretending it didn't happen. I thought it would be better."

"Like what?"

Dean didn't say anything.

"Dean, I'm your brother. You can tell me anything."

"Fine," Dean said, slightly snapping and figuring he was going to regret this.

"I, uh…" Dean stammered, looking at his hands, "I kept hitting on Cas."

Sam started laughing hysterically and Dean stood up abruptly.

"This is why I don't tell you anything!"

"I, but… really?" Sam said, struggling through his fit of laughter. "I mean, just the way you two were looking at each other this morning…"

Dean crossed his arms to add to an intense glare.

"You done?"

Sam attempted to turn his laugh into a cough.

"Yeah, yeah," Sam smiled, "but why ignore it and lie?"

"I think pretending it didn't happen will be better. We can just be friends. That would be easier."

Sam tried not to keep laughing but he couldn't help it.

"Go to school, Sam," Dean said, throwing the car keys to Sam.

Sam raised his eyebrows and Dean nodded.

"You're a good brother even if you're a pain in my ass," Dean said, turning to go into his room for a little bit of sleep.

"Thanks, Dean," Sam said before leaving their apartment.

Dean fell back onto his bed. He tried not to think of Cas and his messy hair… blue eyes… the way he responded to his flirting… how he looked driving the Impala…

He did try but not successfully. He gave up and fell asleep with a smile on his face.

**AN: Thanks for reading! I love reviews, feel free to leave if you like it (or not). Maybe predictions or what you hope will happen?**


	13. New Spot

Castiel was walking home thinking about what happened the night before. He figured if Dean didn't remember all of his flirting than he didn't mean any of it, either. That was probably how he always acted when he was drunk, just flirted with anyone trying to get laid.

_Just forget it and move on,_ Cas thought. It would be stupid to bother with Dean in that way, a guy like that would only hurt him. Cas decided he would just do his job and shut down Dean if he tried anything else. It was for the best.

_The sooner I do my job, the sooner everything goes back to normal._

Cas walked through his front door and was immediately ambushed into a very tight, engulfing hug. It was like being attacked by a python and it was getting hard to breathe.

"CASTIEL!" was yelled into his ear by none other than his older brother.

He couldn't answer without air and Gabriel let go of him but stayed in his face.

"Where the hell have you been? I texted and called for hours, I didn't sleep, I almost called the cops! Fuck, you can't just 'go for a walk' and disappear! I thought you were dead in a gutter."

Cas dug his phone out of his pocket and showed Gabriel it had died.

"My phone died?" Cas's excuse came out like a question. He knew it was lame. He walked around Gabriel to get into the apartment.

"Your… your phone?" Gabriel seethed. Cas turned around and jumped when Gabriel slammed the front door.

"I'm sorry…" Cas said, backing away step by step.

Gabriel charged towards Castiel, yelling that he would kill him for making him worry.

Cas ran around their table and then their couch before dashing into his room and slamming his door.

"CASTIEL!"

"Nope, go away."

"Let me talk to you."

"No thanks, you just threatened to kill me. I'm all right in here."

"Fine. I'll talk through the door," Gabriel reasoned. "You can't do that to me, I seriously thought something happened to you."

"I'm sorry," Cas replied sincerely.

"You're all I got. I can't lose you."

"I know."

They stood on opposite sides of the door in silence until Cas heard Gabriel head to his own room.

Cas spent a good three hours in his room, dozing in and out, until his now charged phone buzzed. He didn't recognize the number.

**Hey meet me and Benny in an hour**, the text read.

**Hello to you too, Dean. Where?** Cas answered right away. He wasn't worried about taking longer to respond because they were just friends. Friends texted back and that's what he would do.

**2 blocks south of the usual**

**Okay.**

Cas spent the next hour mentally preparing himself. It would take everything he had to ignore Dean if he decided to keep flirting like he did last night.

_Just get in the gang, get enough information and you're done and you can forget about Dean_, he told himself.

The more rational part of his brain knew he didn't want to forget Dean but he decided to ignore that part. What the hell did it know?

When Cas showed up at the new location, Dean was already there but Benny wasn't. He was leaning against the wall of the corner store in a red plaid shirt and jeans, already smoking. The sun was hitting Dean's hair making it look more of a light, golden brown.

_He looks good, maybe Jo had a point about the whole 'bad boy' thing…" _Cas thought. He quickly shook that out of his mind as he walked up to Dean. He really had to focus.

"Hey Cas," Dean paused to inhale, "how ya doin'?"

"I'm fine. How are you? You had a rough night. And morning."

Dean cringed.

"Yeah, that wasn't my finest evening. Sorry you had to see that, I know I was difficult when you finally got me home."

"I thought you didn't really remember last night?" Cas said, squinting and tilting his head in confusion.

"Oh, I, uh… don't. Sam helped to fill in some blanks."

Castiel nodded and leaned against the wall next to Dean.

"So," Dean said, rubbing the back of his next, "Benny couldn't make it but I, uh, decided something. I can trust you. I mean, after last night… not many people I hang with would help me like you did, you know?"

Cas didn't say anything. Dean took a drag of his cigarette.

"I'm going to sell to you, Cas."

"Oh. Thanks, I guess."

Cas pulled the twenty out of his pocket that he had been holding onto from the cops to finally buy from Dean.

"Whoa, whoa, whoa. Subtle, man. Like a handshake," Dean said, using his non-smoking hand to make the transaction. Cas put the baggie into his pocket.

"What happened with the cops to make you move?"

"Henriksen, this cop, tried to bust me and Benny a couple of days ago. We got away and decided to come here instead."

"I met Henriksen, the night of Crowley's party."

Dean nodded.

"Right. He's a pain in the ass," Dean said, putting his cigarette out under his boot.

"Where is Benny?" Cas asked. It felt a little weird to be hanging on the street corner without him.

"Got called in to the diner where he works last minute," Dean answered, lighting up another cigarette.

"Should I… go?" Cas asked. He was unsure because he finally bought and didn't know if Dean would want him to stay now.

Dean thought about it as he inhaled. He then took his time blowing smoke out of his mouth, away from Cas.

"Nah," Dean said, turning his head to look at Cas, "you can stay if you want."

Cas let out a small sigh of relief and smiled. Despite what he tried to tell himself earlier, he wanted to spend time with Dean, even just as friends. He hadn't really hung out with anyone this much outside of Gabriel in a while.

It was harmless, right?


	14. Diner

**AN: Hello! Thanks for reading/checking this out! Friendly reminder, Dean and Cas are both twenty years old. (because Dean mentions something that happened in the past and you have reference to how long ago it was.)**

**Enjoy the longer than usual chapter!**

* * *

Dean and Cas stood at the intersection for a couple of hours. Whenever Dean made a sale, Cas stood by and tried not to be too awkward.

A cop car drove by at one point and Cas relaxed only when Dean breathed a sigh of relief because it wasn't Henriksen and they didn't stop.

"All right," Dean said, "I'm all out."

"Oh," Cas said, sounding disappointed.

"That doesn't mean we have to go our separate ways," Dean laughed at Cas's disappointment, "you hungry?"

Cas smiled.

"Where did you have in mind?"

"We could visit Benny at work," Dean suggested with a shrug.

"That sounds like fun," Cas agreed.

"Sounds good. Let me just run inside here and we can go."

Dean walked into the corner store they were in front of and came back a few minutes later holding a new pack of Marlboros.

He ripped the plastic off the cigarettes and threw it on the ground as they walked.

"That's littering," Cas said matter-of-factly.

"Oh no, call the cops," Dean rolled his eyes as he lit a cigarette. He put the pack and his lighter back into his jeans pocket.

"Aren't you scared of getting arrested?" Cas asked. He knew from experience it sucked.

"Nah," Dean said, blowing smoke out into the hot June day, "they can't catch me."

Cas figured Dean knew he meant arrested for selling weed, not littering, and still wasn't phased. He didn't have a response to Dean's arrogant reply but he did feel a slight twinge of guilt because he was playing a role in trying to get Dean arrested.

Cas followed Dean into the small diner that Benny worked at. There were rows of booths along the wall of the door they entered in and stools at the counter and an old-fashioned jukebox in the corner. The two sat themselves, waving at Benny who was working the grill in back.

Before they could order anything, Cas excused himself and went to the bathroom. Once inside the bathroom, he called Officer Mills.

"Castiel, what's up?" she answered, "We haven't heard from you in a while."

"Sorry about that."

"Everything okay?"

"Yeah, everything's great," Cas said, leaving the part out where he maybe had a crush on one of his targets.

"Henriksen hasn't seen Dean and Benny in their usual spot."

"They moved, two blocks south. I was with Dean there today, he sold to me. And others."

"Come to the station later and we'll talk, okay? I have to go, but thanks, Cas," Mills said, hanging up.

Cas left the bathroom and rejoined Dean at their booth.

"I waited to order," Dean grinned.

"Thanks," Cas said, trying not to grin but he couldn't help it. Dean's grin was contagious.

A waitress named Elizabeth came to take their order. Since Cas figured Dean came here a lot, he decided to order the same thing, a burger with fries.

"So, Cas," Dean started, resting his elbows on the table, "I feel like I don't know much about you."

"I feel like I don't know that much about you either," Cas said, trying to spin it around.

"You've seen me shitfaced, met most of who I consider family and have driven my car. That's more than I have on you."

"All right," Cas sighed, "what do you wanna know?"

"Geez, you make this sound fucking terrible! I'm just making conversation, being friendly," Dean said with a laugh, but the way he said friendly, with a pause before it, made it seem anything but.

Cas smiled like he tended to do when Dean laughed.

"Fine," Cas said good-naturedly, "I live with my older brother and I work at the community college."

"Really? Doing what?"

"I work in the library but because it's summer, I don't get many hours. Which is way I came to you guys, I guess," Cas said, adding the lie to explain why he showed up at their corner about a week and a half ago.

"Do you go there, too?"

"Uh, no," Cas said, not caring to elaborate and taking a sip of water. "What do you do, Dean?"

"Besides sell pot?" Dean smirked.

Cas shrugged.

"I'm a mechanic, a damn good one. I work in Bobby's garage, you should meet him."

Cas agreed that he should. As he did that, Elizabeth returned with their food.

"You mentioned before your dad used to work with Bobby?"

"Yeah, used to," Dean said, picking up his burger and looking at it with awe. He closed his eyes as he bit and chewed.

"What happened?" Cas asked, taking a bit of his own burger. He thought Dean was overreacting but it was actually a very good burger.

"He died, drank himself to death on Christmas when I was seventeen, senior in high school. I dropped out with one semester left to work for Bobby full time. I became Sam's legal guardian when I turned eighteen that January," he paused to take another bite. "Not many people know that."`

"Your secret is safe with me, your business is your business. I know I rarely talk about my family."

"Anyone besides your brother?"

"No," Cas responded, biting his burger. Dean took a fry, dragged it through some ketchup and bit it, his eyes not leaving Cas. It was oddly suggestive but so were a lot of things that Dean did because that's how he was.

"Come on, I just told you my life story…"

"That wasn't your life story,"

"You know what I mean."

"Sorry, it's just… I usually never tell people this. Ever."

"Your secrets are safe with me," Dean said, using Cas's words which made him feel comfortable enough to share.

"My parents died when we were young. We bounced from foster care to group home and everything else. Nothing really lasted, it was always too much to handle two boys, especially when one is my brother. He's a piece of work."

Dean laughed at that.

"I should meet him, I've been told I'm a piece of work myself," Dean beamed, "Teachers were always pleasantly surprised to have Sammy after being stuck with me."

"I bet," Cas retorted. Dean stuck his tongue out in response.

"Real mature, Winchester," Cas joked.

Instead of laughing, Dean leaned forward. He was completely serious now.

"I don't even know your last name."

"Novak," Cas smiled.

"Castiel Novak," Dean said. Cas never liked his name as much as he did right then. The way Dean said it sent a thrill through his entire body, warming him up. He knew it was ridiculous, but if Dean was the only one to ever say his name again, that was fine by him.

As they finished eating, they continued talking, eating and laughing. Dean told him about the drag racing Benny mentioned before at the Roadhouse and that it was going on tomorrow night. Cas said it seemed dangerous.

"That's what it makes it fun," Dean winked.

Cas looked down at his empty plate, feeling his cheeks get warm. How stupid was it that Dean could make him blush so easily?

Dean's foot brushed his under the table, making them both jump.

"You have to try their pie, Cas," Dean said after clearing his throat. "I'm going to take a quick smoke break, digest a little and then we'll get some, okay?"

Cas nodded, his brain still a little fuzzy.

Cas briefly checked his phone. Gabriel hadn't texted so he wasn't worried and no call from either police officer. When he looked up, Benny was sliding into the booth across from Cas.

"Hi, Benny," Cas greeted, "on a break?"

"A brief one. How you been?"

"Good. Dean let me in on your new spot and we worked there for a while."

"Worked a new corner? Today?" Benny seemed confused.

"Yeah, he said you had to move spots and you got called into work last minute. I went and then stayed to help, well I just stood there, really…"

"Dean knows I work on Fridays. Have for a while now."

Cas couldn't figure out why Dean would lie. Benny said goodbye only because Elizabeth was holding a stack of orders for him. He left and Cas waited for Dean to come back in.

**AN: So, feel free to let me know if stuff in this chapter was cheesy, cute, stupid... Anything. :)**


	15. Pie

Dean walked back into the diner, carrying his red plaid shirt instead of wearing it over his plain white t-shirt. The shirt outlined his arm muscles very well and Cas was staring until Dean snapped him back.

"Yo, Cas, anyone home?" Dean asked. "McFly?"

Cas squinted his eyes and tilted his head.

"You don't get my _Back to the Future_ reference but you got when Meg called you Clarence?" Dean asked, shocked.

"My brother likes Christmas a lot, I've seen that movie plenty of times and I haven't seen _Back to the Future," _Cas answered before changing the subject, "How are you wearing jeans? It's too hot out."

"That's why I took off the top layer," Dean explained, gesturing to the button-up next to him on his side of the booth.

"Why not just a t-shirt and shorts?" Cas said, looking down at his own red t-shirt and black basketball shorts.

"Oh, sweetheart, I don't do shorts," Dean winked.

Cas was giving him a look and was going to say something but it went unnoticed by Dean whose attention was on Elizabeth who had returned to their table.

"I'm guessing you'd like some pie, Dean," she speculated with a smile.

"I really do come here too much, don't I?"

"Not enough," Elizabeth kept smiling, getting a grin from Dean.

Cas crossed his arms over his chest.

"How about a slice of pecan then?" Dean requested.

"Sorry, Dean. 'Fraid we're all out of pecan," Elizabeth said, her smile faltering a little.

"Damn it," Dean cursed, "everytime. All right, apple then. Cas, how about you?"

Dean turned to look at Cas.

"Cherry, please," Cas ordered. Elizabeth left to get the pie.

Cas tried to avoid looking at Dean.

"What's wrong?" Dean asked. Cas sighed.

"It's nothing," Cas replied. Elizabeth returned with the pie slices from the display on the counter. Dean shrugged and immediately dug in, closing his eyes as he chewed like he did with the burger.

"Dean, what is this?" Cas asked, not touching his pie yet. His arms were still crossed and his eyes fixed on Dean.

"Heaven," Dean moaned, mouth full of pie and his eyes still closed.

"I'm serious," Cas said, trying not to focus on Dean's moan and moving mouth, which was very difficult.

"So am I," Dean said, chewing blissfully.

"Dean."

At Cas's urgent tone, Dean opened his eyes and swallowed.

"What is this?" Cas asked again, finally able to look Dean in the eye.

Dean looked from Cas, down to Cas's untouched slice of cherry pie and back to Cas.

"I call it dessert, Cas."

"That's not what I meant," Cas said quietly, finally taking a bite of his pie. Dean took a small, second bite.

"Then what do you mean?" Dean asked when he finished that bite.

"I mean this, us. What's going on?"

"Two friends having lunch… or dinner, depending on how you want to look at it," Dean said, glancing at the clock over the door of the diner.

"Not everything's a joke, Dean. Can we just talk for a second?"

Dean took another bite.

"I'm not usually the type to talk about this either, but…" Cas said.

"Then why talk about it?" Dean suggested as he ate.

"Because… you can't just flirt with Jo and Elizabeth…"

"Whoa, Cas, what's the big deal?" Dean exclaimed, taken aback.

"It's not, not really… but… You can't flirt with everyone and me too, okay?"

"What do you mean?" Dean's eyes narrowed.

"Benny told me you know he works Fridays."

"So?" Dean asked, finishing his last bite of pie.

"So why bother with just me, taking me here?"

"To get to know you!" Dean refuted.

"You're looking to get laid, just like last night and like always."

"Last night… come on, last night I was drunk," Dean argued, "With Jo, that girl, you... it doesn't count!"

Cas opened his mouth then closed it and narrowed his eyes.

"I thought you didn't remember last night."

"I, uh… shit. Look, Cas, I just thought it would be better to forget it."

"Well, maybe it's not that easy for me to forget. Maybe I didn't mind you flirting with me but then it doesn't really mean anything when you do it with everybody."

"That's not fair…"

"No, it's not fair for you to lead everyone on. Let me guess, you're not very into relationships, right?"

Dean didn't say anything so Cas kept going.

"Just one night stands? No commitments, no strings…"

"You're wrong," Dean said quietly, "I was in a relationship, it ended a couple months ago."

"Did it only last a couple months too, maybe just a couple weeks?" Cas snapped.

"No, a year."

"A… a year?" Cas felt sick, he couldn't have been more wrong.

"Yeah, a year."

"I… I didn't know. Dean…"

"You just assumed," Dean said, getting angry, "because you don't know anything about me."

"That's fine by me," Cas said, standing up. He threw some money on the table and marched out of the diner.

Cas walked to the police station to talk to Officer Jody Mills. He thought Dean was going to follow him out of the diner but he didn't.

The argument was stupid and they both were at fault for different things but how could Dean blame Cas for thinking he never taking relationships seriously, after what he had seen so far? Dean flirted with anyone and everyone.

_A year,_ Cas thought, _holy shit, that's a long time…_

He finally got to the station and quickly found Officer Mills.

"Hi, sorry I was so abrupt earlier. We had a lot going on. What do you got for us?" she said.

Cas handed her the weed and gave her an update on selling with Dean and repeated the new location two blocks south of the old location.

He also decided to mention the drag racing that was going to be happening tomorrow night.

"Really?" Mills asked.

"I guess, they race the other gang, the one that crashed Crowley's party."

"Huh."

"Do you guys know anything more about the other group?"

"No. I'm sorry, Castiel. If we do, I'll tell you."

Cas nodded his thanks and showed himself out.

**AN: Sorry it's been a few days for an update. Even if there are gaps between chapters, I will finish this, no matter what. Thanks for reading, favoriting/following and reviewing. I appreciate it!**


	16. Back in Black

**AN: Have a longer than usual chapter because I'm having a hard time figuring where to break them up! I've already staretd the next chapter and it will be up before you know it. Enjoy!**

That same night, after what happened at the diner, both Dean and Cas headed home to their own apartments. Castiel, after the police station, was feeling particularly on edge.

When he got home, Gabe was cooking.

"You hungry?"

"No, already ate," Cas answered as he shut the front door behind him.

Gabriel checked his watch as he stirred what was in the pot on the stove.

"It's only five!"

"Yeah, well, I ate," Cas said, flopping on his back on the couch.

"Everything okay?" Gabriel asked, picking up on Cas's dejected body language.

"Everything's fine," Cas lied. Gabriel resumed cooking.

The situation was a little different at the Winchesters' place. Dean opened and closed the front door and got two steps into the apartment when Sam asked him what was wrong. He didn't even look up from his homework and books scattered around the table.

Dean sighed and sat at the table with Sam.

"It didn't go well with Cas. He found out I lied about last night."

"I'm shocked," Sam said genuinely.

"That it didn't go well?" Dean asked, raising his eyebrows.

"No, that you're being honest with me and I don't have to wring this out of you."

"Shut up," Dean said with a halfhearted smile.

"What else happened?"

"He says I flirt with everybody."

"You _do_ flirt with everybody, Dean," Sam pointed out.

"Well, he said he doesn't like it."

"Oh."

"Oh?" Dean asked, confused.

"If he's pissed you flirt with other people, he likes you."

"Really?"

"Really. You're bad at this, you're lucky you have me."

"Right. How's it going with Jessica again?" Dean tried turning the tables.

"We're studying together tomorrow," Sam beamed, "just the two of us."

"You should take her on a real date," Dean grumbled, having lost this battle. Sam laughed and Dean stood up.

"Keep studying, nerd. I'll fix you something to eat."

Cas worked for a few hours the next morning, having one thing on his mind.

Dean's race tonight.

Castiel couldn't figure out if he should go or not and wrestled with it the whole day before deciding he would.

Dean was in a similar situation, nervous about the race and if Cas would show up. He even texted Cas to ask if he was coming, but didn't get a response.

The races started at nine sharp. It had gotten dark and was still pretty warm out, but getting cooler.

Most people were standing around the alley either holding a beer, smoking or both. The guys from both gangs were there but keeping a safe distance from each other. The first race of the night was Crowley and Michael. Michael won and the two almost got into a fight after but were pulled apart.

Everyone resumed just standing around and Cas showed up. Dean was leaning on the hood of his Impala, smoking, when he saw him out of the corner of his eye.

It took Dean by surprise how good Cas looked, he was just wearing a black T-shirt and jeans, and he coughed as he inhaled.

"You all right, brother?" Benny asked, smiling as he joined Dean.

"Fine," Dean wheezed.

"Enjoying the view?" Benny asked, looking at Cas. Dean looked over, too. Cas had started talking to Meg.

"Shut up," Dean snapped, continuing to smoke. Benny laughed and went over to join Cas and Meg, saying hi to Meg and shaking Cas's hand. Benny was the only guy in the group who knew Dean was bisexual and would always give him a hard time like only a best friend could.

One of the guys from the other gang was disappearing into an alley with a girl which made Dean laugh a little. Considering how things were with him and Cas, he almost wanted to try something like that himself.

Dean stepped on the butt of his cigarette as two of Michael's guys approached Cas, Benny and Meg. He walked up as Meg left, standing between Cas and Benny and standing face to face with Raphael and Zachariah.

"Oh, look, you guys brought fresh meat," Zachariah taunted, sizing Cas up. Cas didn't seem fazed.

"You drive?" Raphael asked, getting to the point.

"No, but Dean does," Cas responded.

"We know _he_ does," Zachariah sneered.

"You also know he kicks your ass," Benny added. Dean grinned smugly. The people standing around the alley from the rival sides had started to circle up and watch.

"Zac and I want to see what you're made of," Raphael jeered at Cas.

"Can't help you, I don't have a car," Cas said, turning to walk away. Raphael grabbed his right shoulder and spun him back around and left his hand there.

"You don't want to do that," Cas growled. Dean was actually impressed, the dude was kind of intimidating when he wanted to be. It was also kind of hot but that wasn't the point.

Raphael glared but didn't move his hand so Castiel pushed it off for him with his left hand.

That was all the provocation Raphael needed and he shoved Cas in the chest with both hands, hard. It sent Cas back three steps who immediately responded with a shove to Raphael's chest, harder. Dean and Benny moved to intervene but Cas snapped at them to back off.

The first punch was thrown by Raphael and it was dodged by Cas who retaliated with a solid right hook that hit Raphael square in the jaw. He fell to the ground.

Dean and Benny held Cas back as Zachariah helped Raphael up.

"This isn't over, someday you'll pay for this," Raphael said, standing and holding his face.

"Maybe. But today, you're my little bitch," Cas returned.

As the gangs wandered apart again, Crowley came up.

"You're definitely tougher than you look, I'll give you that," he said. Cas nodded his thanks.

"Nice hit, Clarence," Meg winked and Cas smiled.

At that, Dean called Cas over by his car. He was leaning on it and smoking again in his olive green Henley shirt, sleeves pushed up, and jeans.

"So that's not flirting?" Dean accused, smoking and not caring if the smoke went towards Cas.

"Why, you jealous?" Cas replied.

"Damn, one fight and you think you're hot shit," Dean laughed, "you even have crappy one liners. His little bitch?"

Cas shrugged and leaned on the Impala next to Dean.

"I mean… it wasn't really…"

"Joke, Cas. I was joking."

"Oh, right…" Cas said, looking down.

"Why don't we hang out after this, talk?" Dean suggested.

"I don't think that's a good idea, Dean."

"Why not?"

Cas could think of several reasons why not but kept his mouth shut.

"Come on, Cas. I can't be that bad."

Cas smiled. Of course he wasn't, he was the opposite, and that was the problem.

Cas was going to protest when he saw Michael walking towards them. Dean put out his cigarette and crossed his arms.

"What?" was Dean's simple demand.

"Uriel wants to race you," Michael said coolly, crossing his own arms.

"Can he even see straight? Pretty sure I punched him pretty hard last week," Dean smirked.

"That's why he's challenging you."

"Why isn't the bastard doing it himself, errand boy?" Dean mocked.

Michael tensed at that, which Dean hoped he would.

"He's already in his car," Michael answered, fighting to stay level, "he figured you'd say yes."

"He's right, let's fucking go!" Dean exclaimed, turning towards his car.

Before he got in, he whistled to call his guys, and Meg and Ruby, over. He let them know he was racing Uriel and got a loud cheer in response.

"Place your bets now, boys and girls and I'll win you some money," he yelled arrogantly.

They dispersed to get ready to watch.

"Be careful, Dean," Cas said as Dean got into the Impala.

"Me? You just started a fight, man!"

"I'm serious."

"All right, all right. I have a bet for you."

"What is it?" Cas wondered.

"I win, we talk. Got it?"

Cas thought about it for a second before giving in and shaking Dean's hand through the window of the car.

"Wish me luck," Dean winked. He blasted "Back in Black" and drove up the alley to meet Uriel at the start. They were going to race down to were Cas and everyone was standing and waiting.

As Dean drove over, Cas was mentally kicking himself. He knew it was a bad idea to spend time with Dean, any more than was necessary for his undercover job. On the walk over to the race, he told himself to avoid Dean.

How could he though? Dean was hard to ignore.

The race started and was over almost as soon as it began. Despite Uriel being in a newer looking Camaro, Dean kicked his ass. There wasn't much time for celebrating because police sirens could be heard closing in fast. Everyone dropped what they were doing and ran or drove away.

"Get in!" Dean yelled through the passenger side window, pulling up next to Cas.

He didn't argue and climbed in. Dean stepped on it and they were gone.

**AN: As always, thanks for reading/reviewing/favoriting/following. I appreciate all of it!**


	17. Second Opinion

They didn't drive far from the race before stopping at what looked like a crappy elementary school with a playground in even worse condition. The whole place looked run down and slightly creepy.

Dean parked the Impala on the blacktop between the school building and playground instead of the parking lot.

"I don't think you can park here, Dean."

Dean just laughed and got out of the car. Cas sat and just looked at the sad state of where they were for a moment before Dean asked him if he was coming.

Cas, against his better judgment, got out of the car. He joined Dean who was sitting on the hood of the Impala, using the windshield as a backrest. Cas was extremely careful as he climbed up to join Dean.

"What did you want to talk about Dean?" Cas asked. He was all too aware of how close he was to Dean at the moment. Their legs and shoulders were inches apart.

"How come you didn't answer my text earlier?" Dean questioned. It sounded simply curious, not accusatory.

"I didn't know if I was coming or not," Cas said, looking at his hands in his lap.

"You could have said that."

"I'm sorry," Cas said, looking up at Dean who met his gaze.

"It's cool, man," Dean replied, "forget it."

The two sat in comfortable silence, looking up. There was maybe a single star to be seen because of all of Chicago's light and air pollution but it was still nice to enjoy the summer night.

"Dean," Cas spoke up as he wondered about something, "we talked about your dad, and you don't have to answer if you don't want to but…"

"What about my mom?" Dean guessed, looking at Cas again.

Cas nodded. Dean was quick on reading Cas.

"She died when I was four in a house fire. That's why we moved into the shithole apartment I grew up in and still am stuck in."

"Was the house in Chicago, too?"

"Yeah," Dean responded, "They moved here after they got married. My mom's parents didn't like my dad so they ran away."

"Where were they from originally?"

"Lawrence, Kansas."

"Interesting," Cas mused. Dean shrugged.

"Tell me something about you," Dean said, eager to change the topic.

"Like what?"

"Anything."

"I got expelled from the fancy high school my foster parents were sending me to."

"No shit?" Dean exclaimed.

Cas laughed.

"I'm serious. After a stint in juvie for my brother's weed I had and shoplifting for him, plus getting in a fight to protect my foster sister, Anna, they booted me. Became an emancipated minor after that family didn't want me and my brother anymore."

"How old were you?"

"Sixteen."

"Wow. Fucking crazy, you are just full of surprises," Dean said with awe, looking at Cas with his intense eyes. Even in just low streetlights, they were magnificent.

Cas cleared his throat and looked down.

"So, you seem smart," Cas said, now the one to switch up the topic, "how'd you manage to get mixed up with Crowley and them?"

Dean laughed but it was a little bitter and different from his normal, contagious laugh.

"Nah, Sammy's the brain of the bunch, always has been. Those guys hounded me during high school, trying to get me to join. Sure, I'd buy from them, I knew I wasn't doing much after high school anyways, but I didn't want to get mixed in. I kept saying no until my dad died."

Cas patiently listened, waiting for Dean to continue and explain. Dean took a deep breath, looked up at the sky and kept talking. Cas watched his face as he talked.

"Apparently, Crowley gets the businesses on his turf to pay for protection from the other guys, Michael's crew, in guys joining or money. If not, you get hurt. My dad and Bobby had been paying them off but the garage was hurting when we lost him. We didn't have that kind of money."

Dean looked down at his hands as he scratched at the edge of a thumbnail.

"So, I joined. Otherwise, they would have hurt Bobby or tried to get Sam to join. I had no choice."

"I'm sorry, Dean," Cas said, after a pause to make sure Dean was done.

"Thanks, Cas. Only Benny, Bobby and Crowley know that's why I joined. I keep Sam in the dark, too."

"To protect him," Castiel said, trying to reassure Dean.

Dean scoffed.

"That's what I tell myself. I just don't want him to think I'm a lowlife gang member, you know? Hell, if my parents knew…" Dean shook his head.

Cas reached out and grabbed one of Dean's hands.

"It's okay, Dean. You're not a machine."

"I just go through the motions sometimes, though, and shut everyone out. But with you, I feel like I can open up, you know?"

"I do. You know about as much about me as my brother and I've only known you for a week a half," Cas smiled, squeezing Dean's hand. He returned the smile and the squeeze.

Dean's eyes darted down and landed on Cas's lips before returning to his eyes. Cas's heart beat quickened and his face got warm as Dean leaned in.

Their faces were about an inch away and Dean's eyes were starting to close when Castiel interrupted him.

"Dean," he said softly. He didn't move his head back at all or let go of Dean's hand. Dean opened his eyes but didn't move his head back at all either.

"Give me a reason not to and I won't," Dean said just as softly.

Cas opened his mouth to say something, anything, but his mind was only focused on Dean. His eyes, his freckles, how close he was, his body heat, his lips…

Cas's eyes stopped on Dean's lips. He wondered what it would be like to kiss them so he decided to find out. He closed the gap between them, pressing his lips gently on Dean's.

Dean tasted a little like cigarettes but Cas didn't mind. The rush he felt through his entire body, blood pumping and roaring in his ears, and hot all over was overwhelming that.

He let go of Dean's hand to put one on his shoulder and the other at the back of his neck. Cas pulled him closer as he ran his fingers through his hair, which was incredibly soft.

They broke for air. Castiel took a couple of slow breaths then opened his eyes. Dean was grinning next to him.

"You're a good kisser," he said, "but I'll need a second opinion."

Dean began kissing Cas again, whose hands hadn't moved, and gradually moved on top of him. The kiss grew more heated as Dean was straddling Cas. Dean slid a hand under Cas's black T-shirt, making Cas moan into Dean's mouth. Dean kissed with more fervor, grabbing Cas's face and pushing his tongue into Cas's mouth.

Everything stopped as a bright light caused them to break apart. Dean got off of Cas and they both put a hand up to shield their eyes.

"What the fuck?" Dean cursed.

"Evening, gentlemen. Hope I'm not interrupting anything."

"Henriksen, you dick," Dean spat.

"Watch it, Winchester," Henriksen said, all joking aside and lowering his flashlight out of their faces. Cas was pretty sure both of their faces would have been a sight, messy hair and too red lips. He was glad to lose the spotlight.

"You boys mind telling me what you're doing loitering here, parked where you're not supposed to be?" Henriksen continued, looking at them both.

"Told you," Cas whispered.

"Shut up," Dean snapped.

"You," Henriksen said, looking at Cas, "I thought I told you to be more careful after the party?"

Cas didn't say anything but if Dean didn't know any better, he'd say Cas looked scared.

"All right, we're leaving. We get it," Dean said snidely.

"Good. I've seen enough of you two for a while," Henriksen said with a smug smile of victory. He stood by his squad car and waited for the boys to get into the Impala.

As they drove away, Cas still looked a little spooked.

"You all right, Cas?" Dean asked, looking at him as he drove.

"Yes, fine… I just, I should go home," Cas stumbled on his words, seemingly distracted.

"Home? I mean, whatever you want but you've tangled with that asshat before and…"

"Please?" Cas pleaded, "just take me home?"

Dean had never seen Cas like this and took him home. Cas said a hasty goodbye and got out of the car at his apartment. As a bewildered Dean drove away, Cas ran up the stairs three at a time. He slammed the front door of his dark and empty apartment shut and leaned against the door.

Castiel jumped as his phone rang and he read the caller ID.

_Henriksen._

Cas cringed then answered.

"Hello?"

"Get down to the station. Now. I'm not asking."

_Click._

**AN: Thanks for being so patient everyone, I know most fics don't make you wait this long for a little bit of action! :)**


	18. Under Pressure

**AN: Sorry it's been a week. I'm back at school and busy so I'll do my best to keep going as fast as possible. Thanks!**

Castiel's stomach was twisting and turning as he walked the several blocks to the police station to meet with Officer Henriksen.

When he walked through the front door, Henriksen was standing in the lobby talking to the officer behind the front desk. That officer looked at Cas and said something to Henriksen who then turned to look at Cas.

His smile faded as his eyes landed on Cas.

"Follow me," Henriksen said shortly.

Cas headed down the hallway behind Henriksen and got the feeling like he was going to the principal's office.

In the interrogation room that Castiel was getting really sick of, Officer Mills was already sitting at the table. Henriksen joined her on one side and Castiel sat across from them.

Cas looked back and forth between the two cops before looking at his hands in his lap.

"Castiel, what happened tonight?" Jody Mills asked. Henriksen opened his mouth but closed it when Mills put up a hand.

"I, uh…" Cas started. He looked up, took a deep breath and continued. "I was at the race and Dean wanted to talk. I said it was a bad idea so we made a bet. If he won, we'd talk."

"Did he win?" Henriksen asked with a slight sneer.

Cas glared at him until Officer Mills encouraged him to continue.

"Yes, he won," Cas snapped, "so we went to the playground at the school and we… talked."

"It wasn't just talking when I showed up," Henriksen pointed out.

"What is your problem?" Cas said in a low growl.

"You're kind of screwing the investigation if you're _screwing_…"

"Okay, okay," Mills cut Henriksen off, "Look, we're just concerned that you're getting too close which would complicate things."

"I bought the weed, told you about drag racing and I can still do the damn job."

"But Winchester? Really?" Henriksen jeered.

Cas was understanding Dean's dislike for the man.

"Consider remaining more unattached, Castiel. It'll be easier," Mills said.

Cas nodded and left the room.

The next few days, Cas followed the advice given to him by Officer Mills. Dean sent a couple texts to check on him which Cas opted not to reply to. He wanted to, he did, but decided to add some space between the two of them. Preferably, they would be making out on the hood of the Impala again without anything interrupting them.

Cas worked on Sunday, briefly, and again on Monday. There was one text from Dean and a call on Tuesday. Cas felt worse and worse ignoring Dean and finally texted him on Wednesday afternoon to ask if they could meet up.

**Cas: You free today?**

**Dean: Yeah, sellin with Benny same spot. **

**Cas: Now?**

**Dean: An hour**

**Cas: Ok.**

When Cas arrived at the corner, only Dean was there.

"Hello, Dean," Cas greeted.

"Cas," Dean said testily, focusing on his cigarette.

"Where's, uh, Benny?" Cas asked, tentatively.

"Inside," Dean said, sounding very uninterested in talking to Cas, still not looking at him.

"I get you're pissed, Dean, I do…"

"Do you?" Dean snapped, suddenly very interested and angry, glaring at Cas.

"Let me ex…"

"Explain? Explain how you've been ignoring me? I thought we had a good time, at least I did, and then… complete 360 and you ignore me. Did…" Dean shifted into a more vulnerable look, "did I do something wrong?"

"What? No, Dean, I had a good time, too… Really, but…"

At that moment, Benny walked out of the store.

"Cas, hey brother, where've you been?" he smiled, shaking Cas's hand.

"Uh, work, mostly…"

"Speaking of… I really got to get going to work myself. Bye, Dean, good to see you, Cas."

"You too, "Cas said as Dean said goodbye to Benny.

"Let's go for a drive," Dean threw out. Cas agreed.

The first minute or so was tense and silent. Dean sat straight up as he drove instead of leaning back like on Saturday. Both hands were also on the wheel instead of just his right hand on the top and his left out the window.

"So… you were saying you had a good time Saturday?" Dean said, trying to make light of the situation.

"I did, honestly, it was…" Cas sighed remembering their kiss.

"It was something else," Dean laughed, leaning back just slightly and his shoulders relaxing.

Cas laughed too. It was a good description.

"Then, I thought… I thought I messed up. I'm not good at this stuff, usually, so…" Dean stammered.

"You didn't mess up. I needed time to just…" Cas struggled to get as close to the truth as possible. "Think, I guess? I know that sounds lame…"

"It doesn't, I get it. We haven't known each other long, it was a big step. But, we need to communicate better, I suppose," Dean said, turning to smile warmly at Cas as he drove.

"Yeah," Cas agreed.

They drove around until they got hungry and decided to meet up with Benny, who had only been covering a few hours for someone, at the Roadhouse.

Dean and Cas grabbed a table and waited for Benny to arrive. Jo took their order, giving a quick hello to Cas before focusing on Dean. To Cas's surprise, he had toned down the flirting considerably. There was less smiling, less winking…

"Dean," Cas began.

"What's up, Cas?"

"I noticed you didn't flirt with Jo very much tonight."

"Well, you kind of got upset last time I did that, so…"

It was hard to tell in the dimly lit space, but Cas might have seen a slight pink tint to Dean's cheeks as he looked down and rubbed the back of his neck.

Cas smiled.

"What are you smiling about?" Dean said, looking up.

"Oh, nothing."

Benny showed up.

"What'd I miss?" he asked, sitting down. Dean moved a little to his right to give Benny room, making him closer to Cas's left around the small table.

Cas and Dean shared a look then quickly looked away.

"Nothing, we, uh, just ordered," Dean said, still a little flustered.

Benny looked between the two of them but then lost interest when Jo returned with their food. He swiped a fry from Dean's plate before it even touched the table.

"Hey, get your own!" Dean snapped, swatting Benny and pulling his plate in towards him.

"Good idea. Jo, I'll have the same," Benny said. She nodded and left.

Cas and Dean both dug in right away. When Benny's food came, he was distracted enough, Dean decided, that he could move his leg so that their knees were touching. Cas gave him a sideways glance and smiled just a little before looking back at Benny, who was all over his own burger.

"Damn, Benny, it's like you can't grill your own somewhere," Dean quipped.

"Food is better when you don't have to make it yourself," Benny responded.

The rest of the time while they ate included sideways glances between Dean and Cas, accompanied by shy smiles and one bumping the other's knee while they were about to take a bite and having to try not to laugh.

Jo came to deliver their check and instead of talking to Dean, she turned to Cas.

"Can I talk to you, Cas?"

"Sure," Cas said warily and didn't move.

"Maybe outside?"

"Uh, yeah, sure."

Dean and Benny looked just as confused as Cas felt he did as he followed Jo out of the bar.

"Cas, what's going on?" Jo demanded as they stopped just outside the door of the bar.

"What do you mean?"

"I mean with you and Dean, what's going on?" Jo asked, crossing her arms over her chest.

"Nothing…"

"Bullshit. I saw you guys at the table, that's not nothing."

"Jo…"

"It hasn't even been a week since you told me you didn't see him like that and now? What the hell, Cas?"

"I didn't…" Cas was going to say he didn't lie to her, he didn't see Dean like that. But that was then.

"Never mind. I should be used to this by now, you saw him here last time. You know how he is. I hope he at least treats you better than all the bimbos," Jo shook her head and walked down the alley next to the Roadhouse.

**AN: Some shout out thanks to some reviewers...**

**cherrytops82 - Your 'continue soon's are much appreciated.**

**superchiwo - Thanks for your multiple reviews y besos tambien.**

**deanloveshizpizzaman - Your review was super sweet :) Thanks!**

**CastiellaWinchester94 - I always enjoy your reviews on my fics :)**

**lindsayd16 - Aw, thanks!**

**Dancerline - Sorry for confusions and freak outs haha. Your reviews pointing out what you like are helpful and I enjoy them. :)**

**Thanks all for reading/reviewing/favoriting/following as always. See you soon, I promise!**


	19. Ready for Love

After Jo walked away, Cas was left standing there feeling pretty shitty. Jo had a point about how Dean acted around women usually but if tonight was any indication; he could turn down his flirting. He hadn't been lying to Jo about his feelings for Dean, at the time, and it was really shocking how everything was turned around from one kiss.

Cas sighed. His brain basically shut down when he thought about that kiss, he had gotten reprimanded at work for spacing out because of that kiss… How could he not constantly think about it, though? Dean on top of him, his hand hot against his skin under his shirt…

"Cas, hey, you okay?" Dean said, stepping out of the door to the bar. The daydream couldn't compare to seeing Dean in front of his own two eyes.

"Uh, I…" Cas stammered, focusing on Dean's lips, which made his brain continue to short circuit. Dean was standing right in front of him and was close enough to touch but Cas resisted.

"Where'd Jo go?" Dean asked, snapping Castiel into focus.

"She got pissed, saw us at the table… Stormed off down the alley. Guess we weren't too subtle," Cas explained.

"No," Dean laughed, "I guess not. Benny made a comment, too."

Cas wasn't terribly surprised, Benny wasn't an idiot and they had been pretty obvious.

"Do you, um… I mean… Do you care?" Dean asked, rubbing the back of his neck, which made Cas smile. "That people see?"

"You rub the back of your neck when you get flustered," Cas stated.

"I…" Dean stopped, "I do not!" He lowered his hand indignantly.

"You do."

"Fine, maybe I do, but…" Dean looked at the ground.

"It's cute," Cas pointed out.

"It… what?" Dean asked, looking up and meeting Cas's eyes.

"You heard me," Cas said simply. He stepped forward and quickly wiped the startled look off of Dean's face and answered the question if he cared that people saw them by kissing him. After all, they were on a sidewalk in Chicago where plenty of people could walk or drive by.

Cas didn't give a shit. He had Dean in front of him and he wanted to kiss him again since Dean dropped him off Saturday night.

Cas put his hands on Dean's hips and pulled him closer while turning him to make sure his back was to the wall of the Roadhouse and without breaking the kiss, backed Dean against the wall.

"Fuck, Cas," Dean mumbled into Cas's lips before passionately kissing him and easily guided his tongue into Cas's mouth.

Cas leaned against him more, pressing his knee between Dean's legs. It made Dean tighten the grips he had both in Cas's hair and on his hip. Cas began to move both of his hands up Dean's shirt. His skin was soft and hot over a pretty nice stomach and chest.

Dean pulled his head away a fraction of an inch to laugh softly and say, "If you're getting hands-y, maybe we should move this somewhere else."

"Where do you suggest?" Cas asked in a low, sexy voice that made Dean kiss Cas before answering.

"My car," Dean said, his mouth against Cas's neck as he placed hot kisses. Cas leaned his head back and kept his hands under Dean's shirt.

"Yes, your car, Dean. _Now_," Cas said, the last word with enough urgency to get Dean to push Cas back a step, grab his hand and pull him away from the wall towards the Impala.

In the driver's seat, Dean was having a hard time starting the car and then driving because Cas was practically in his lap.

"Cas, holy shit, we're going to get pulled over…"

The bench style of the seat allowed Cas to be against Dean's right side completely. He was kissing Dean's neck and a hand was in Dean's soft hair and the other was on his thigh.

Both of Dean's hands were steadfastly at ten and two on the wheel and his knuckles were white.

The car jerked violently to the left and almost into oncoming traffic as Cas moved his hand up Dean's leg.

"Fuck…" Dean moaned, "we need to pull over."

He pressed the gas pedal down further and they quickly got to the alley the drag racing took place in behind the store without Cas distracting Dean enough to crash.

As soon as the car was parked and off, Dean was on top of Cas completely, pressing him against the seat.

"You made me almost crash my baby," Dean pouted. Cas had to laugh.

"It's fine…"

"_She…"_

"Does it matter, Dean?"

Dean looked down into Cas's amazing blue eyes and forgot everything else but the guy they belonged to.

As they made out, they each worked the other one's shirt off. There was a pause as they both kind of just raked their eyes over inch they could see, taking in the muscles and skin of the other one.

Dean began to undo Cas's jeans while they kissed again but was interrupted.

Cas's phone was ringing in his front pocket.

"Fuck, seriously?" Cas groaned.

Cas quickly dug it out of his pants and looked apologetically at Dean before answering.

"What?" Cas snapped. Nothing came to mind that should be breaking this up right now.

"Hello to you, too, Cassie," Gabriel answered, sounding bemused.

"Really not a good time, Gabriel," Cas said, focusing very hard to keep is voice steady but his voice hitched on his brother's name. Dean hadn't bothered to stop what he was doing and had moved Cas's pants down and was rubbing him over his boxers.

"Yeah, well, I wouldn't be calling if I didn't have to."

"What's wrong?" Cas had to bite a finger to stop from making a sound as Dean kept touching him.

"I, uh… got arrested. Think you can help a brother out?"


	20. Precinct Again

**AN: Still doing the best I can to get chapters written and posted as fast as I can. Enjoy!**

"Seriously?" Cas asked, not entirely surprised Gabriel had gotten arrested but extremely annoyed at his timing.

The shift in Cas's voice to legitimately concerned got Dean to finally stop moving his hand over Cas in his pants.

"Unfortunately," Gabriel said, "can you come get me? What are you doing anyways? You sound kind of out of breath."

"Nothing," Cas sighed, smacking Dean lightly on the arm when he laughed. Dean was still very close to Cas and could hear the entire phone conversation.

"Really? Because…" Cas heard a cop snap that his time was up.

"I'll get you," Cas said reluctantly, "bye."

Gabriel didn't even say goodbye as the phone was taken from him. Cas heard him shout indignantly before the line went dead and hoped he didn't get himself in more trouble.

Dean was smiling above Cas.

"So, do I get to finally meet your brother?" he joked.

"I think I should deal with this on my own, Dean," Cas said. Dean pouted.

"Come on, Cas!" Dean said and crawled off of Cas. Without Dean on top of him, Cas pulled his pants back up and started searching for his shirt.

"I think it ended up in the backseat," Dean smirked.

Cas looked and there his shirt was. He turned, got on his knees on the bench front seat and leaned over the seat to grab it, very aware of Dean's eyes on him, specifically his ass.

"Do you have to stare?" Cas said as he sat back down, facing forward. There was no way he would miss an opportunity to make Dean Winchester blush.

Dean in fact did start to turn a little red and rubbed the back of his neck which made Cas laugh as he put his shirt back on.

"Shut up," Dean said but with a small smile. "Do you want a ride to the police station?"

"Sure. Thank you, Dean," Cas answered, "I'm sorry about this."

"It's not your fault. I understand the troublemaker older brother… That's been me my whole life," Dean smiled as he started the car after he put his own shirt on.

"You can meet him… eventually," Cas said as they drove, "Just not tonight, okay?"

"I get it," Dean said.

When they pulled up to the police station, Dean asked if he could see Cas tomorrow.

"Sure," Cas beamed. He couldn't wait.

Cas walked inside the station and was met by Officer Mills.

"Hi, Castiel," she greeted.

"Hello. Where's Gabriel?"

"With Officer Henriksen," she replied.

Cas tried not to wince too obviously but Mills saw and smiled.

"Oh, he's not that bad," she tried.

"I just really don't think he and my brother will get along," Cas explained.

They headed back to a different interrogation room than Cas was used to. Cas followed Mills into the room.

"Cassie! Great to see you," Gabriel said, way too enthusiastically for the situation.

"I'd like to say the same, Gabriel."

"Oh, don't be like that…"

"Is he being charged with anything?" Cas demanded of Henriksen.

"No, not officially… but," he started.

"Then can we go?"

Henriksen gave Mills a look before answering.

"Fine. I wasn't getting anywhere with him anyways."

Gabriel got up with a triumphant look on his face and walked out the door with Mills. Cas was going to follow but was stopped by Henriksen's hand on his shoulder.

"Castiel, wait."

Cas didn't answer, instead he focused on putting all of his hate into a glare and roughly snapping his shoulder out of Henriksen's grip.

"Let me take one guess where you were tonight. Or more specifically, who you were with."

"Take as many guesses as you like, it's still none of your damn business."

"I'd be a little more respectful if I were you," Henriksen said smugly then leaned in, "I can still try my best to get you and your brother thrown in jail."

Cas turned and walked out of the room. Henriksen called after him as he retreated down the hallway to leave.

"Get me more information about the gang, Novak, or you're both screwed!"

"Cassie…"

"Don't start, Gabriel," Cas answered as they walked home.

"Don't you want to hear my side?"

"Your side? You got arrested, there isn't a side to that."

"Don't you want to know why?"

"Not really," Cas said. He was being very short with Gabriel, borderline rude, and it probably had to do with the fact that Gabriel had interrupted his time with Dean.

"You don't want to talk about me, fine… what were you up to tonight?"

Mental images and sounds crept into his brain at the exact wrong time and he could feel his face get warm.

"Nothing," Cas replied quietly, watching his feet as he walked.

"My ass. You were getting some! I know that face. Granted, it's usually on other people and not you…"

"Gabriel," Cas said warningly.

"Fine, fine, don't give me the details. Just know I'm happy for you."

"Thank you."

Castiel didn't really want to mention how it was a bad idea to keep doing what he was doing with Dean and that he should do the "just friends" speech tomorrow if he sees him. And Cas did want to see him, really badly, but seeing Dean made him do crazy things, like pushing him against a wall and kissing him, when he shouldn't.

If there was ever a definition of a relationship being called "it's complicated," this had to be it.

They walked in silence until they reached their apartment and both went to bed.

The next day, Cas woke up at about ten and he already had a text message.

**Dean: When can I see you?**

Cas tried to stop his insides from flipping around, the warmth spreading to his fingertips and the goofy grin spreading across his face but it doesn't help. It all happened anyways.

**Cas: I'm free all day.**

**Dean: Good, we should meet at the corner then go to the store and meet the other guys there after.**

**Cas: What time?**

**Dean: Couple hours**

**Cas: Ok.**

Cas had been sitting up on his bed to type and flopped back when he sends the last message. How is he supposed to stop kissing Dean when he's by him? Or to stop thinking about him all the time or worrying about if he's okay and just wanting to be with him?

Cas knew one thing with absolute certainty. The realization hit him and he screamed into his pillow.

He was fucked.


	21. Friends?

Cas showed up at the usual corner a couple hours after he texted Dean who was already leaning on the wall and smoking. It was hard not to smile seeing Dean in such a comfortable position, trying to give off his bad boy vibe when Cas had seen some of his softer side.

"Hey," Dean said, still propped on the wall.

"Hello, Dean," Cas replied with a smile.

"Benny's working so it's just us today," Dean said as he took a drag of his cigarette.

Cas wished his heart rate didn't jump at that fact. It made what he needed to do that much harder.

"Dean, about yesterday…"

"It was great, we should do it again sometime," Dean said, his smile all teeth and confidence.

"It _was_ great but…" Cas sighed then looked at the ground.

"But what, Cas?" Cas could practically hear the worry in those three words and the fading smile.

"It's just… I don't think the timing is right for us, you know? And I think maybe we rushed this and it will fade just as fast. I'm not good at relationships or dating, I've only really been in one…" Cas rambled and couldn't seem to stop, "I don't want our friendship to suffer because we kind of skipped the friendship stage originally?"

He ended his rant and accidentally made the last sentence a question.

"So…" Dean said slowly, putting his cigarette butt out as he thought, "You're saying we should just be friends?"

"Yes," Cas said, glad Dean seemed to get what he said.

Cas then felt really bad because Dean looked so upset.

"I don't mean forever, things can change, but…"

"Kind of… slow things down… a lot?" Dean asked, looking Cas right in the eyes. Castiel really didn't want to see such hurt in those beautiful eyes.

"Yes," Cas agreed, "but things could pick up again."

"Friends with potential?" Dean asked. Cas knew he was trying to diffuse the tension with a joke but his small smile was telling enough he wasn't really laughing.

"Sure, I like that," Cas smiled. Dean's smile grew more genuine when Cas smiled.

The two remained on the corner, tense at first, but gradually the awkward small talk became just friendly chat. They talked about work and their brothers mostly, Dean even told Cas about Jess and how he wanted Sam to ask her out already.

They stopped selling for the day and got into Dean's car to head to the store the gang usually hung out at. As they drove, Cas focused most of his energy on _not _thinking about happened on this seat of this car just last night. The seat against his back, Dean on top of him, hot kisses on his neck…

It was impossible.

Dean seemed lost in thought as well.

"What are you thinking about, Dean?

"Oh, nothing," he said, but the hand that grabbed the back of his neck gave him away.

"You're thinking about last night," Cas said, a statement not a question.

"What… no, I, uh…" Dean tried hiding but looked at Cas and gave up. "Yeah, I was. How'd you know?"

"The hand on the back of the neck thing you do."

"Dammit, Cas. You really know me that well already?"

Cas shrugged.

"You're such a great mind reader, what am I thinking about now?" Dean teased.

Cas figured it was lunchtime about and they had driven past the diner Benny worked at so he made an educated guess.

"Pie?" Cas tried.

"Yeah, but that was easy. I'm usually thinking about pie."

They both laughed as they pulled into the store's parking lot.

As they got out, a few hands were thrown up in greeting but most of the guys didn't change what they were doing. Most had cigarettes and were sitting on hoods of cars or leaning against them.

"Hello boys," Crowley greeted in his signature accented drawl.

"Crowley," Dean nodded.

"Cas, have you met everyone?" Crowley asked.

"Most, I think, but it's hard to remember everyone's names," Cas admitted.

Crowley rambled off all of their names as he pointed them out. Cas had met them all but had forgotten which name went to who so this helped.

There was Jake, one of two black guys, but the one who survived being shot; Gordon was the other. Alastair and Azazel who were both very creepy looking, Dick and his Hispanic buddy Edgar were there too.

"So, you all sell?" Cas asked, trying to make conversation because their conversations had stopped when Crowley did introductions and they were still staring at him.

"What are you, a narc?" Edgar asked.

"A… what?" Cas asked, confused.

"A cop or a rat to the cops," Dean said to him before addressing them all. "He's not a narc."

Cas gulped. This was what he was afraid of. They knew he was fake, that he wanted them all arrested. Well, except Dean.

The guys still seemed unsure of Cas.

"He socked Raphael, remember?" Crowley said, "He's on our side. Take it easy. As I recall, none of you lot brought anyone like Dean here did."

Cas looked confused.

"We were looking for people to join when I asked you to come to the party. You keep coming back because you're awesome," Dean explained in a quick, hushed tone to Cas.

Castiel was okay with that. He didn't really want any of these guys to be his friend. Again, except for Dean. But he would prefer if they didn't want to kill him.

Not much went on with these guys here besides an argument between two that almost became a fight before they cooled off.

When they were done, Dean offered Cas a ride home.

"Okay," Cas agreed.

Dean stopped in front of Cas's building.

"We should hang out outside of selling and away from those fucking idiots," Dean suggested.

Cas raised his eyebrows and opened his mouth but Dean kept going.

"As friends. Friends do stuff… just hang out. Maybe get food or whatever."

"I'd like that," Cas said and Dean visibly relaxed.

"Okay," Dean grinned, "I'll see ya, Cas."


	22. Jitters

In the remaining weeks of June, Dean and Cas hung out as much as possible. They kept it strictly friends even though Cas knew Dean wanted it to be more. It was obvious in how close he would be to Cas as much as he could and the fact that there was usually a text from him waiting when he woke up. They would usually just to be to make plans for the day or a silly fact or a movie quote that Cas wouldn't understand. Anytime Cas didn't understand a reference, Dean added the movie to a "Cas Must Watch" list.

Their plans would either be at the corner or one of their apartments, mostly Dean's, to watch those movies. Cas had so far seen all of the Star Wars movies and liked them as well as the most recent Batman trilogy. Occasionally, they'd eat where Benny worked and avoided the Roadhouse because of Jo and her temper. Eventually, Cas and her would work it out.

Once Sam finally asked Jess out, Cas and Dean took him out for ice cream the night before the date was planned to celebrate.

"Glad you finally did it, Sammy!" Dean cheered. The three of them were sitting outside on the curb in front of the tiny little ice cream shop, Dean in the middle. Cas and Sam both smiled.

"Yeah, me too," Sam agreed with a shy smile.

"What's the big plan for the date?" Cas asked.

"Just dinner and a movie," Sam said proudly.

Dean and Cas smiled at each other but the context of the conversation made it a little awkward and they both looked away.

Cas sighed inwardly as Dean and Sam kept talking. He was afraid being just friends would make things awkward between them. This wasn't the first time, either. Watching movies, Dean would sit kind of close on their couch or keep flirting or just basically stare at Cas when he thought he wasn't looking. Cas picked up on all of it but had to fight not to return those feelings.

Cas's master plan was to get information on the gang, everyone but Dean, get them arrested and sent away so Dean would be free and they could be together. He knew it was lofty but he could dream.

"Cas?" Dean asked. Cas turned and Dean was looking at him expectantly.

"What?" Sorry," Cas apologized. He didn't mean to space out for so long.

"I said, Sam's going to go hang out with some friends so I offered to drive you home," Dean explained.

"Oh. Oh, yeah. Thanks."

Cas said bye to Sam and wished him luck on his date tomorrow. Sam's friends walked up and they all walked away.

When they got in front of Cas's apartment, Dean put the car in park and turned to face Cas.

"Cas, I…" Dean took a deep breath, "I was wondering if maybe you'd… you'd want to go get dinner and see a movie one night? With me? Or ice cream, just us? I mean, if you want…"

"I would want to, Dean," Cas assured him quickly. He knew putting yourself on the line was hard.

"Oh," Dean smiled, "Oh. That's great!"

Cas couldn't help but laugh at his excitement.

"Can I ask you something, Cas?" Dean wondered, face turning kind of serious but his eyes still lit up from eagerness.

"Yes, Dean?" Cas asked softly.

"Can I… can I kiss you?" Dean asked, looking more vulnerable than ever and even a little afraid. Cas never meant to make Dean feel scared to kiss him but it just couldn't work with them, not yet. That didn't mean they had to stay _completely _platonic, right? Cas said it could be more. And he wanted more…

Cas nodded and they both leaned in, Cas inching a little closer on the seat to make it easier.

It was slow and cautious at first and the most gentle out of any of their kisses so far. It stayed soft and sweet and was quick.

Cas was disappointed when it ended and kept his eyes closed as Dean moved his head back a little.

"I'm sorry, it's just… I pretty much always want to kiss you and it's been hard not being able to."

"You don't need to apologize, Dean," Cas smiled. "I enjoyed that a lot." Even if he was talking about physical need, not necessarily feelings, Cas appreciated Dean was opening up a little with him.

"So, that can maybe happen a little more?"

"I think so."

"Okay. Cool," Dean grinned.

Cas said good night and headed upstairs.

The end of June and into July was pretty much the same; hanging out, selling and watching movies. There was just more kissing.

Henriksen would occasionally text asking about information regarding the gang. Cas let him know the names of everyone in the gang, two of which Henriksen didn't know about and that kept him occupied for a while and off of Castiel's back.

Finally, Dean texted and made plans to officially take Cas on a date. Cas had seemed to respond quickly and eagerly and Dean was interpreting it as a good sign.

The day of the date, Dean woke up a nervous wreck and his stomach was in knots and he couldn't eat breakfast.

Sam raised his eyebrows as Dean pushed his plate away at their table. It was a Saturday and Dean needed to go to work soon.

"Dean…"

"Sam, I'm already on the verge of puking."

"Nice. Look, going on dates isn't that hard. Didn't you go on dates with Lisa?"

Dean only had messy dark hair and blue eyes on his brain and honest to God had to think long and hard about who Sam was talking about.

"Uh, Lisa? No, we didn't… really go _out_ much. Kind of stayed in?"

Sam nodded, if he got what Dean was implying, he didn't let on.

"Okay, well, can I give you advice?"

"You're going to anyways so… shoot."

Sam had to make a bitchface before answering.

"Relax, okay? First of all, do that. If he didn't like you, he wouldn't have taken care of your drunk ass that one night. Also, you should bring him flowers. That would be nice."

Dean nodded and felt like he should be taking notes.

"Okay. Relax. Flowers. Okay." Dean's eyes were focused on one spot on the table and he was still very tense.

"You're not relaxing."

"Go to school, Sam," Dean quipped.

"It's Saturday, Dean."

Dean snapped out of it and cracked a smile.

"Got to keep you on your toes, keep you sharp."

"I got straight A's, again, I'm pretty sharp."

"Quit bragging," Dean said through a wide grin. Of course he got all A's. One of the many reasons he was so proud of him.

"Just be yourself and it will be great."

That line kept running through his head as he got ready and went to work.


	23. Date Part 1

**AN: I binge wrote a lot so even though I might get busy, I can still update almost (hopefully) daily. At least for a while. Enjoy! **

Cas was shut in the one bathroom of the apartment he shared with Gabriel and had been for quite some time. He couldn't get his hair to do anything right.

Apparently, it had been too long.

"Castiel, what are you doing? Are you getting ready for a hot date?"

"Go away, Gabriel."

"I have to use the bathroom, come on!"

Cas opened the door to the bathroom. He had a simple light blue button up shirt on with the sleeves rolled up and dark jeans. It was weirdly cool for a Chicago July night.

"Damn," Gabriel whistled, eyeing him up and down. "You _do_ have a hot date!"

"None of your business," Cas pushed past Gabriel out of the bathroom.

"Who is she, can I meet her?" Gabriel pried.

"No you can't meet him," Cas said, correcting Gabriel and answering his question.

"Why can't I meet him?" Gabriel pouted but going with the flow and accepting the curveball. Sure, Gabriel knew Cas liked guys too but the swift response like that was nice.

Cas had to smile. Moments like this he remembered why he cared for his brother so much.

"CAS AND SOME DUDE SITTING IN A TREE…" Gabriel bellowed as he shut the bathroom door. "K-I-S-S-I-N-G…"

Castiel shut his door to help block out some of Gabriel's awful singing.

Moments like _this_ were when he remembered why he wanted to strangle his brother.

Part of Dean's day flew by because he got to work on cars. Technically, it was work but it didn't feel like it. If he won the lottery tomorrow, he would still show up at Bobby's shop to work on cars. He'd also bring a huge check to thank the old grouch for everything he's done for him and Sam.

Dean slid in and out from under cars, popped under countless engines and sang the whole time he did it. Bobby let Dean listen to whatever he wanted in the garage as long as it didn't bother him in the office. Dean went through side after side of AC/DC, Led Zeppelin and Metallica tapes.

"All right, Bobby, I'm out," Dean grinned, ear to ear, standing in the door of Bobby's office.

"What are you so happy about?" Bobby grumbled.

"If you must know, I have a date tonight!"

"No kidding? Who with?" Bobby said from behind his desk. He sounded like he actually cared, too. The gruff man could be a softy sometimes.

"You don't know him but I'll bring him by the shop someday. See ya Bobby!" Dean practically ran out of the shop to his car.

Bobby barely got his hand up to flick his hat in a goodbye before Dean was gone.

"Idjit," he muttered.

Dean had almost the entire contents of his closet dumped on his bed. Nothing looked good enough.

"Dean, it's getting late…" Sam stopped in Dean's doorway, glancing at Dean's bed.

"Really, Dean?" Sam asked with a silly smile.

"Shut up and help me pick something," Dean demanded.

Sam quickly grabbed a white shirt to go under a mostly yellow plaid button up with a pair of pretty faded jeans.

"Done. Now go. Don't forget the flowers!" Sam said, his turn to command.

"How could I forget?" Dean mumbled. The flowers were on their living room table, Dean had picked them up after work and he grabbed them on his way out of the apartment.

"Bye, Sammy!" Dean called before running down the hall and down the stairs out to his car.

Dean drove like a maniac to get to Cas. He was lucky enough to get a spot pretty close to the apartment building and parked. He ended up being early and figured he would surprise Cas and show up at his door.

This way, Dean figured, he can put the flowers away before we go.

Dean mentally patted himself on the back for that one as he snuck in behind someone with a key into the building. After a pause at the mailboxes to learn where Cas lived, he power walked over to the stairs and took them three at a time.

At Cas's door, he paused, remembered Sam's advice to relax… and knocked.

After a minute or so of shuffling around behind the door, Cas opened the door.

"Dean," he said, surprised.

"Hi," Dean breathed. He got up here quickly but Cas looked good and that was making the air seem in short supply as well.

"I, uh… These are for you," Dean said, handing the flowers to Cas.

"Wow. Thank you, Dean, they're lovely!" Cas said, taking the flowers and trying to hide his face with them. There was no way he wasn't blushing right now.

Once the flowers were settled, Dean motioned that they should go.

"Bye!" Castiel shouted back to his brother.

"What? He's here? Shit! I wanted to… damn it, hold on…" It sounded like Gabriel tripped over something in his room and started swearing more.

"Let's go," Cas said, unable to hold back a grin.

They could hear a shout of, "He brought FLOWERS?" as they walked down the hallway.

"I do like the flowers a lot, Dean," Cas said, eyes on the buttons above the elevator as they waited.

Dean smiled. "Sam might have helped with that one…" he admitted.

**AN: Shout out to some reviewers.**

**cumberlovin: Hope you catch up on sleep, glad you like it :)**

**rascal: Thanks for the reviews and more BAMF Cas is in the works!**

**Anyone else, feel free to tell me what you think of this story, what works/doesn't... Thanks!**


	24. Date Part 2

They got to the restaurant and the conversation never dulled. It was a slightly fancy Italian place that neither of them had been to called Giuseppe's**.** Dean even pulled out the chair for Cas to sit down in.

There was talk of Cas's and Dean's jobs and when that got old, Dean asked Cas about school.

"You didn't finish high school, right?"

"Right," Cas said, eating the amazing warm bread that kept coming as they waited for their entrees.

"Me neither. I've been thinking... we should get our GED's! I mean, if you want... we could do it together," Dean said, sipping his Coke. He hadn't wanted to try his fake I.D. here and risk getting caught while out with Cas. That would have been more embarrassing than getting caught with Lisa by her ridiculously strict father.

Cas seemed to contemplate the idea while finishing his slice of bread.

"I think we should," he agreed. Dean smiled. Something about Cas made him want them to do this together. It would be good for them.

"Then what would you do?"

"Probably take some English classes at the college that I work at."

"English?" Dean asked with raised eyebrows. He could have guessed that, considering that Cas worked in the freaking library, literally surrounded by _books. _

"What, not your forte?"

"_School_ wasn't my forte. I'm surprised I didn't get _kicked_ out before I dropped out."

"But you're smart."

"A smart-ass, maybe…"

Dean twirled the pasta in front of him that came while they were talking and shrugged.

"You are smart, Dean. You'll get your GED very easily," Cas said honestly. Dean knew Cas believed it and he appreciated that.

"Well, it wasn't just the smart thing. I would have a hard time getting homework done or studying. I always had to try to work or take care of Sam…"

"What about your dad?" Cas asked nervously. Dean didn't seem to like to talk about his dad much.

"He wasn't around a lot," Dean said, pausing to eat some pasta. "He was a mess since Mom died. He drank and wouldn't be much help or disappear then come back, saying he tried rehab or some bullshit. Bobby and Ellen helped look out for us and I always took care of Sam, still do. It's my job."

"The weight that must have been…" Cas said, not even imaging how Dean, or anyone for that matter, could balance all of that.

"It's fine," Dean said, clearly wanting to change the subject.

"But…"

"Really," Dean said. It wasn't mean but it was definitive. That conversation was over. Cas nodded and continued to eat his own pasta.

"What do you want to do with English, Cas?" Dean said, much gentler now.

"I love writing. Books, poems, everything. I like watching people, you know? Seeing what they're like, what they do. Then writing what I see or what I pretend their life is."

Dean couldn't help but smile. He never saw Cas light up like this and he was glad he found something they could talk about that made him this animated.

Even as they ate in comfortable silence, Dean continued to smile and moved his foot next to Cas's under the table, hidden by the long tablecloth.

"Why are you smiling, Dean?" Cas asked, now smiling, too.

"I'm just happy," Dean said, leaving it at that. It was more than he'd normally share. "Why are you?"

"Because you were smiling. I usually smile when you do, it's contagious."

The remainder of the meal consisted of a shared piece of chocolate cake, only because they didn't have pie, and Dean laughing when Cas managed to somehow get some frosting on his nose. Dean reached across the table with his napkin to wipe it off which made Cas blush like crazy.

When the bill came, there was only a slight argument. Dean insisted he pay because he did the asking out, Cas tried to pay for his half and finally Dean ended the argument.

"You can pay next time, Cas."

Dean realized the weight of what he said, implying a second date, so he just continued to tend to the bill, now beet red. Cas shyly smiled and drank some of his water.

* * *

At the movies, it didn't take long for them to start holding hands. It wasn't the both-go-for-the-popcorn-at-the-same-time thing either. Cas literally asked if they could and he looked so cute and of course Dean said yes.

Some of the movie is lost to the two of them, more so Dean, because they're both wrapped in thought of what this means for them. It's an actual date, they both knew that, but where do they go from here?

Cas looked over and saw worry scrunching up Dean's face and reached across with his far hand, the one not holding Dean's, to place it on his cheek to guide him into a kiss. It was quick but did the job. Then, Dean was smiling and relaxed.

Castiel insisted he could walk to his door on his own but Dean was stubborn as hell and walked him to his door anyways. This allowed Dean to get what he had wanted all night which was a good night kiss from Cas in front of his door.

It was longer than the one in the movie theater and just got _really_ good when Dean had to go before it got out of hand. Cas had started opening his mouth to deepen the kiss and Dean knew it could escalate into something Cas didn't want, at least not yet, so he respectfully stepped back.

But it was still perfect and they were both all smiles as they parted ways.

* * *

Dean came home to Sam sitting on the couch, waiting up even though it was getting close to two in the morning.

"Well?" Sam asked.

Dean, who literally hadn't stopped smiling since he kissed Cas good night, struggled to form words instead of repeatedly replaying the kiss in his head.

"It was… awesome."

Sam grinned as Dean smiled all the way to his room and shut the door.

Those were all the details Sam needed. When he got fewer words out of Dean than that normally, he knew this was different.

_Cas_ was different and Sam had only seen them together twice.

He just hoped his brother was smart enough to see that, too.

Dean had been trying hard to get Sam and Jess together without even meeting her. Sam promised himself he would help make sure his older brother would be happy.

And Cas seemed to be the way to make Dean happy. The ridiculous, smile-y, float on air happy that he just saw.

Sam smiled to himself, shook his head and went to bed.

**AN: Hope you liked it! Thanks for reading, I always appreciate it!**


	25. Surprise

It got to mid-July and Officer Henriksen wasn't happy with how much Castiel had done as an informant. Cas had nearly forgotten about his job because his time and focus was all Dean.

Cas only found out his displeasure when Henriksen called him while he was at Dean's and he ignored the call. Instead, he made out with Dean on his couch while they had some movie on in the background.

When Cas finally and reluctantly left Dean's because Dean had work and called Henriksen back, it had been over two hours and several missed calls.

"Novak, I swear if you were with…"

"Why did you call?" Cas cut him off with a sigh. Henriksen's rants about Dean were getting old.

"Can you…" Cas could tell that he was struggling to find the right words, "can you _please_ come down to the station? Officer Mills and I would like to speak with you."

Cas had to hold back a laugh at how Henriksen was speaking carefully and through his teeth. Cas would bet on pain of never seeing Dean again that Mills was standing right next to him making him be nice. And he wouldn't make that bet lightly.

"Sure," Cas agreed. Henriksen said nothing and just hung up.

At the station, a cup of water was waiting for Castiel as he sat, as usual, across from the two cops.

"Castiel, thanks for coming," Mills began.

Cas nodded as he graciously drank the water. The weather was finally realizing it was July and started to act accordingly. It was freaking _hot_ outside.

"We were wondering if you could get us more information than you have," Mills asked, sounding a little cautious.

"Specifically, the locations where the other guys sell," Henriksen said but practically in a civil tone.

Cas figured this was why he was nice on the phone and he got water. He was being buttered up but it didn't matter. Cas couldn't call them out on it.

"I could, sure," Cas said. He kind of had to, didn't he? There was no way he was going to jail or letting Gabriel go either if he could help it.

"Thanks," Henriksen said, almost in pain by being polite.

Cas had to leave the room before cracking up and getting in trouble.

Cas and Dean sold on their corner with Benny the next day. This was only slightly disappointing to them because they weren't alone but Benny was nice enough to go into the store and buy a Coke to give them some time.

They used it wisely. Dean kissed Cas, pressing him against the wall and tasting like cigarettes when Benny came back and announced his presence with a small clearing of his throat.

"Sorry," Dean said with a shy smile to match Cas's.

"No, you're not, brother," Benny laughed. "And you don't have to be."

Dean was grateful for Benny and he was growing on Cas, too.

The three of them relocated to the store's parking lot to join everyone else loitering around.

Benny, Dean and Cas stuck to staying by the Impala and everyone else kind of just gave them space.

"Where does, uh, everyone else sell?" Cas asked. Dean and Benny both gave him a look.

"Just curious," Cas said defensively. Dean shrugged and they told him.

Between the two of them, they could tell Cas the streets where they sold in pairs. Alastair and Azazel weren't far from Dean and Benny's corner. Gordon and Jake were to the west by a little and Dick and Edgar were further south. Crowley just supervised everything.

"But he still gets a cut?" Cas asked, struggling to remember all three intersections. He would have to remember them and text Henriksen right when he got the chance.

"The biggest," Dean said bitterly.

"Hey, you guys coming to Crowley's?" Jake asked as he walked up to the car, cutting off the conversation.

"Another party?" Benny asked.

"You know it," Jake answered.

Dean looked at Cas who shrugged.

"Yeah, probably," Dean responded.

Cas had to smile a little because Dean checked with him and seemed like he only wanted to go if Cas went.

That was fine by him.

* * *

The Saturday that Crowley was planning on having another party, Cas woke up to a text from Dean.

**Dean: What are you doing today? I got Bobby to give me the day off.**

**Cas: Nothing. Why, do you have something in mind?**

**Dean: Yes but it's a surprise. I'll be at your place soon.**

**Cas: Okay.**

Cas didn't try to type out his feelings because it was impossible to put them into words. There wasn't anything to say but "okay." How do you text that seeing a message from Dean already made his day and he was warm and basically _electric _all over? Dean had a day off and he wanted to spend it with _him._ Cas grinned like an idiot and could only guess at what Dean had in mind.

Dean showed up in the Impala as Cas waited on the front steps of his apartment building. Instead of pulling over on the street to pick Cas up, he went and parked. When he walked back, Cas must have looked confused and Dean laughed.

"Cas, you gotta trust me a little, man. It's gonna be fun!" Dean exclaimed.

"Where are we going?" Cas asked as they started to walk down the street.

"You'll see."

Cas pouted.

"Oh, all right, I'll tell you one thing. We're starting on the train."

"That's still very vague, Dean."

Dean laughed.

"I told you already, it's a surprise! Don't you like surprises?"

"Not particularly."

"You'll like this one, I promise."

Cas looked over at Dean as he walked and saw sincerity in those wonderful eyes that set him at ease. He'd follow him anywhere, explanation or not.


	26. Wanted: Dead or Alive

Cas and Dean walked all the way back to the train after the fireworks were over above Navy Pier.

The finally got there and were both pretty tired and rode in mostly silence. Cas rested his head on Dean's shoulder and couldn't remember ever being happier. After being bounced foster home to foster home through most of his childhood and having the only constant in his life be Gabriel, this was a nice change.

But for how long?

Henriksen's plan was to get Dean, Benny and the rest of them arrested. Then what? Cas needed to figure out how to make Henriksen happy enough and keep the people he cared about out of jail. There was a more than likely chance it would go poorly like everything else in Castiel's life had so far.

"Cas, you okay? You seem tense," Dean observed. They were almost back to their stop.

"Yeah, I'm fine," Cas said, sitting up to look at Dean, "Just a little tired but today was amazing."

Dean grinned ear to ear. He was adorable when he got excited, Cas decided.

"Great! I'm glad you had a good time. I did too."

They reached their stop where they started the whole adventure and got off the train.

"Do you want to go to Crowley's?" Dean asked. The party had kind of slipped Cas's mind. It was pretty hard to remember other people existed when he was with Dean.

Cas thought about it. He wanted to spend more time with Dean and he didn't mind if this was how they did it.

"Sure," Cas agreed. He shot a quick text to Gabriel to let him know that he was going to stay out so he didn't worry.

Dean suggested they drive after so much walking that day so they headed back to Cas's apartment to get the Impala where they left it.

As they walked, Cas easily laced his fingers with Dean's who smiled shyly as he did.

They walked and talked about what they liked most at the Taste of Chicago when Dean suddenly let go of Cas's hand.

"Shit," Dean muttered.

"Dean, what's wrong?"

Dean didn't have to answer before Cas found out what was wrong.

"Well, well. Look who it is."

Raphael and Uriel crossed the street and headed right towards Dean and Cas.

They were still out of earshot at the moment and Dean leaned over to Cas.

"When I say run, we go in opposite directions and right to Crowley's," Dean said in his ear. Cas nodded.

"What are you boys up to?" Uriel asked as he and Raphael of them blocked their path on the sidewalk.

"Nothing. Now get out of our way," Dean demanded.

"Now that's not how you want to talk to us, Winchester," Raphael snapped.

"Why the fuck not?" Dean said, attempting to look bored with the situation.

"Because," a voice said behind Dean and Cas, "you're severely outnumbered."

Cas and Dean turned to see Michael and Zachariah blocking their path from the other direction.

"Maybe, but we can still take you," Cas said, attempting bravery when every instinct told him to run. Run fast and run far. He stayed put, holding his ground until Dean gave the word.

The four rival gang members laughed at Cas's false bravado. Dean gave him a look that was trying to stay brave as well but his eyes showed his fear. The situation was going south and they had started to close in.

"Now!" Dean said. He took off up the sidewalk, brushing past Uriel and Raphael.

Cas sprinted the other way, narrowly avoiding being grabbed by Zachariah.

_Fuck, fuck, fuck_, Cas thought with each of his pounding footsteps.

Zachariah and Michael had followed him, he could hear them, but he didn't care. He was just hoping and praying to whatever or whoever would listen to keep Dean safe. If they got him but Dean was okay then Cas wouldn't care.

After a few unexpected turns and detours, Cas seemed to have lost the two on his trail. He started to make his way to Crowley's, now only walking.

As he kept walking, he heard a sharp cry of "There he is!" from behind him and began to run again without even looking behind him.

It might have been stupid but he guessed Crowley's would actually be safest. There was safety in numbers right? Also, the guys he was running towards hated the guys chasing him so he figured they would help.

He got to the party and saw Crowley on the lawn.

"Cas, what…"

"Michael… chasing…" Cas said, slightly out of breath.

Cas didn't need to say anything else. Crowley simply whistled and Benny, Dick and Edgar sauntered over from the porch. They stood next to Cas as Michael and Zachariah caught up. They met on the sidewalk in essentially a staring contest.

"Well?" Crowley asked them. It was clear five to two was terrible for the two unwelcome guests and they began to walk away.

Crowley looked extremely smug and turned to give Cas a nod. Dick and Edgar headed inside and Benny stood next to Cas.

Zachariah and Michael stopped in the street to talk and were might by Raphael.

_Where's Uriel? _Cas thought._ Where's Dean?_

The second, of course, was much more important. Cas needed to know that he was okay.

Benny was talking to Cas but he wasn't listening. He was listening to the guys in the street.

"Where's Uriel?" Michael asked in a hushed tone, aware that Benny and Cas weren't far away.

"He…there was….met up with…" Uriel talked much quieter than Michael and Cas couldn't hear him very well. Whatever he said seemed to make Michael and Zachariah happy and that made Castiel's stomach churn. If those goons were happy, it could not be good.

The three continued to talk and then walked away after throwing oddly satisfied grins at Cas.

_What could they be smiling about? _Cas thought.

"Benny, Dean didn't come here did he?" Cas asked, beginning to panic.

"No, I figured he was with you," Benny answered.

"He was, we got surrounded by four of them and split up. We were supposed to meet here," Cas explained.

Benny shook his head. "I'm sorry, brother, he's not here."

Cas pulled his phone out and called Dean.

There was no answer and Cas had to sit down on the curb.

_Dean, where the hell are you?_


	27. Bad Moon Rising

Cas sat on the curb in front of Crowley's by himself, worrying about Dean. He tried calling him again but there was still no answer. Benny had gone inside to make sure Dean hadn't come to the party and somehow slipped past him.

As Cas was thinking the worst, he was yanked to his feet and spun around very aggressively.

"Who the fuck do you think you are?" Alastair snapped. He and Azazel were in Castiel's face.

"What…" Cas asked, confused.

"You know what we mean, don't play around," Azazel said, his gaze creepy as always.

"I don't, so explain it to me or go away," Cas said, annoyed. He really didn't have time for petty arguments with these idiots when he didn't know if Dean was okay.

"We sell on our corner with no problem for a long time and then you show up and we got problems. Henriksen tried busting us today! He's never been to our corner," Alastair finally explained.

"I don't know anything about that," Cas said. It was a half-truth. Sure, he told Henriksen _where_ they sold but what he did with that information was up to him.

"Don't lie," Azazel yelled as he swung quicker than Cas could blink.

Cas fell to the ground, his cheek throbbing and black dancing at the sides of his vision. He wouldn't have guessed Azazel could hit that hard. When Alastair punched him in the jaw that was a little less surprising that it would hurt that bad.

He tried to get up but that only got him a swift kick to the side and he fell again. A couple more punches and kicks and Cas was ready to give up. Each hit he was hoping would knock him out.

"Hey," a familiar voice yelled, "let's make it a fair fight."

Cas found it hard to see because of the slight swelling of one eye and the borderline unconsciousness he felt. But he had to fight, he had to see…

"Dean," Cas said, barely audible. He was pretty sure it was Dean but he couldn't be sure.

"I'm here, are you okay?" Dean said, crouching down and grabbing Cas's face with both hands.

"I'm…" Cas coughed, which added to the pain along his ribs, "fine. Are… they gone?"

"Yeah, they don't want to fight me, I could take them both," Dean smirked.

Cas managed a laugh without too much pain. The classic Dean Winchester cockiness never failed.

Castiel finally managed to get a good look at Dean. He focused despite the only light coming from a streetlight and the party. Dean had a black eye and blood on his face that was hard to tell where it was coming from. His shirt sleeve was torn and there was blood on his arm that was slowly drying but made a line down to bruised and bloodied knuckles.

"Dean, you look almost as bad as I probably do," Cas said, smiling as wide as his hurt mouth would let him.

"No way, I'm sure I look great," Dean said, helping Cas up.

"What the hell happened?" Benny had finally come back.

"Nothing, nothing…"Dean said, brushing it off.

"When you two have a lover's spat, you really go at," Benny joked.

"Hilarious, Benny," Cas said dryly.

"Uriel and a couple others got me. We're going to get out of here," Dean said, "I'll catch you later."

Cas couldn't help how the jolt of excitement went through him.

"Where are we going?" Cas asked, ready to go anywhere Dean wanted. Dean and Cas began to walk down the street. They could both walk on their own but each were clearly in pain.

"I'm taking you home," Dean said and winked with his good eye.

* * *

"Dean…Cas, what… are you okay?" Sam asked as they walked through the apartment's door. He was on the couch but jumped up and turned the TV off as they clambered in.

"We're fine, Sammy. Could you just grab the first aid kit?" Dean asked.

Sam sighed and went and got it from the bathroom like it was routine. Dean and Cas sat next to each on the couch, probably closer than was necessary.

"Why are you still awake?" Dean asked, getting stuff out of the first aid kit.

"I was worried about you," Sam said, "and for good reason, apparently."

"I'm fine," Dean insisted, "this isn't the worst that has happened."

Cas looked at Sam.

"This isn't the worst that has happened," Sam confirmed. Cas hated seeing Dean hurt and knew that even worse would be awful to see.

"We could use some of the frozen peas, too," Dean said, grabbing some hydrogen peroxide and cotton swabs.

Sam got them and set them on the coffee table.

"What can I do?" Sam asked.

"Nothing, it's fine," Dean said again, getting impatient. "Seriously, it's late. We can take care of each other. Right, Cas?"

Cas was too busy blushing to answer.

"If you're both going to get all cute, I'm out, goodnight," Sam said.

"Night, Sam," Dean and Cas said together. Their eyes didn't leave each other and they both laughed a little.

"Ew," Sam said, shutting his bedroom door, making Dean and Cas laugh more.

"Okay," Dean said, looking where to start first. He silently cleaned Cas's face up, wincing when Cas did even though it didn't hurt Dean, until Cas spoke.

"I wish they hadn't gotten you, I wish they caught up to me," Cas said.

"Don't be ridiculous, I'm glad they got me," Dean said, pausing as he cleaned. He handed Cas one of the bag of peas to put on his swollen eye. "But it didn't really do anything, you still got beat up. What's their problem?"

"They said Henriksen crashed their corner today."

"And?" Dean kept moving the cotton along Cas's hurt face.

"And they blamed me," Cas explained.

"But you didn't have anything to do with that! I swear, next time I see them…"

Cas put a hand up and grabbed Dean's wrist, stopping Dean from what he was doing.

"Dean, it's okay," Cas said softly, looking right at him.

"No, it's not…" Dean said, still angry.

Cas, even though it kind of hurt, kissed Dean. He could feel the anger melt out of Dean. It was quick but nice.

"It's okay," Cas said again.

**AN: Sorry to leave such a cliffhanger last time... JK I'm not I love those :) Thanks for waiting! And reading/reviewing/favoriting/following. As always, I appreciate it. See you soon, hope you liked this chapter!**


	28. More Than a Feeling

"How is it okay, Cas?" Dean asked. "We're both beat to hell and I just wanted today to be special." Dean got a little sheepish with the end and looked down, his voice slightly trailing.

"It's okay because _you're_ okay, Dean," Cas said, putting a hand under Dean's chin to lift his head up. "I was so worried when you weren't at Crowley's… I thought…"

"That something happened?"

"Yes. Really bad and… I can't stand that, thinking about losing you? I had to…"

"You had to what?" Dean wondered, grinning with that mischievous glint in his eyes. Cas dropped his hand from Dean's face.

"I had to sit down on the curb, are you happy?" Cas admitted and Dean laughed. How could he laugh?

"I'm sorry, how is this funny?" Cas demanded. "I thought something was terribly wrong… and…stop laughing!"

"It's not…" Dean said, trying hard to stop laughing but Cas's face was all scrunched up and now he had crossed his arms. "Not really, you're just adorable, that's all."

Cas's face softened and he could feel it get warm. The two of them tried to look anywhere else but it was hard when they were so close on the couch.

Dean finally met Cas's eyes.

"I feel the, uh, same, though, you know? Seeing Alastair and Azazel ganging up on you? I'm…well, kind of shocked I didn't hurt them."

Cas knew talking about feelings was not something Dean preferred to do and Cas knew this meant a lot for him to admit all of this.

"I know, Dean," Cas smiled. The pain in his face and ribs was subsiding. Still hurt, just not as much. He was lucky Dean got there when he did. "And this was still the best day ever."

"Well, then you must have had some shitty days…" Dean said, almost starting to lean in for a kiss. He had meant it as a joke but a dark look passed over Cas's face who had started leaning too until Dean finished talking and froze in place. Dean quickly remembered all about Cas and growing up in foster care and his trouble with police before and that he most likely _did_ have shittier days. _Much_ shittier days.

"Fuck, Cas…I'm sorry, I didn't mean…"

"It doesn't matter, Dean," Cas said as he stood up. "It's getting late."

Cas started to go towards the door but Dean got up as well and grabbed his wrist.

"Dean," Cas said, in a similarly warning tone that he used when talking to Raphael. Dean let go.

"Cas, I'm sorry, honestly. Sometimes, I'm an idiot and I don't think before I speak. Please stay?" Dean was practically begging at the end but he didn't care. He couldn't let Cas leave angry, especially not in the middle of the night. What if the guys who beat either of them up found him and Dean wasn't there to protect him?

Cas sighed and checked the clock above the apartment's TV. It _was_ late.

"Fine," Cas said, sounding exhausted. "Your couch was actually pretty comfortable the last time I slept on it."

Dean turned to get Cas an extra blanket from the closet to hide his disappointment. How did he manage to fuck this up? It had been such a great day and if it had gone better and Dean didn't open his stupid mouth, Cas would be sleeping in his bed. Maybe nothing would have happened, maybe something would have but Cas would have been close to him and not on the fucking couch.

Dean handed Cas the blanket and Cas noticed that it was the same one he used before.

"Goodnight, Dean," Cas said with finality that Dean took as his cue to leave, not saying anything as he went in his room and shut the door.

Cas sighed. _Why do I always overact? He was joking, he doesn't realize…what I've been through….he hasn't had it easy, either…_

It didn't matter, not anymore. Cas fell asleep quickly, a tight frown on his lips.

Dean found it impossible to sleep. He was replaying the entire day in his head, from texting Cas this morning for the surprise date until Cas icily told him goodnight. There was no doubt it was a great day.

Mostly.

Dean groaned and rolled over. How could he be so stupid and careless?

_What else is new_, he thought bitterly. _Another thing in your life you messed up. _

He continued trying to shut his brain down but from self-hatred to thinking of if Cas was in his bed now, it was clearly not happening.

In the dead silence of the apartment, there was a noise, sort of like a whimper. Then something that was more like crying or whining.

"Cas?" Dean asked too softly for anyone but himself to hear. Dean got out of bed and slowly walked to his door, still hearing what he guessed was Cas having a nightmare.

He opened his bedroom door and saw Cas on the couch and he guessed right about the nightmare. Cas was on his back, muttering incoherently and had tears silently streaming down his face.

"Cas!" Dean said, trying to wake him up as he practically ran over to him. Cas kept freaking out in his sleep.

"CAS!" Dean said, as close to shouting as he wanted to get with Sam sleeping. He shook Cas's shoulder as well.

Cas woke up and immediately tried to push Dean away and swung at him without realizing who it was.

"Hey, hey, Cas," Dean said, grabbing Cas's fists and sitting on the couch right next to Cas's side, "it's okay, you're okay, I'm here. I've got you, Cas."

The words were soft and comforting and Cas began crying some more and fell into Dean's arms. Dean let Cas cry into his shoulder until he was no longer shaking and the tears dried up.

Cas sniffed. "I'm so sorry, Dean, I…"

"Cas, don't. I should apologize, earlier…"

Their faces were close and they only needed to whisper.

"I overreacted…"

"I…oh. Are we…are we?"

"We're okay, Dean." Cas said, still seeming pretty shaken up but his small smile held warmth, warmth for Dean. Dean grabbed Cas's face and wiped away some of the tears with his thumbs. Cas leaned into the touch and closed his eyes as Dean kissed his forehead. Dean rested his forehead against Cas's.

"Dean," Cas said, very softly and tenderly.

Dean opened his eyes and met Cas's that were very huge, blue and wet at the moment.

"Can I…um, can I sleep with you tonight?" Cas asked, seeming almost nervous bringing it up.

Dean also figured Cas didn't mean _sex_, just actually sleep and that was fine with him.

"Of course," Dean said. He led Cas into his bedroom but was a little awkward. He hadn't had anyone is his own room for a long time, especially not anyone he cared about this much. Did Cas prefer a side of the bed…or?

"Cas, do you…" Dean turned around to ask.

Dean's question was cut off when Cas's mouth was on his. The kiss was all heat and passion and Cas kicked the door shut behind them and pushed Dean towards the bed.

"Cas…" Dean breathed. He should stop, now wasn't a good time. It would be taking advantage of him if this continued. Cas looked at him with something that could only be described as lust, his eyes raking up and down Dean's body.

It was _hot _and Dean couldn't resist.

"I need you, Dean," Cas said, before kissing Dean again and walking them back to the bed. The mattress hit the back of Dean's knees and he fell backwards with Cas on top of him.

Dean used every inch of will power he had to put a hand on Cas's chest and push up enough to get Cas to stop forcefully making out with him.

"Cas," Dean said, "now might not be the best… unnh…" He was going to say "time" but Cas had starting sucking on his neck and moving his hips against Dean's, "the best… time," Dean continued, fighting hard to think of words and not Cas's hands that were starting to take Dean's shirt off.

"Now is a great time, Dean," Cas whispered into Dean's ear, successfully removing Dean's shirt then removing his own. "I need a distraction."

"I don't…" Dean temporarily lost his train of thought as Cas's lips pressed down on his, "don't just want to be a distraction," he finished when Cas paused.

Cas stopped moving his hips and wandering hands.

"You're not _just_ a distraction, Dean. I've wanted this since the night in your car that my idiot brother interrupted."

"Me too but… tonight's a good night?" Dean asked, brow furrowed.

"Yes. We had an amazing date today and that's what I'm choosing to remember. If you want, we can make this day even better."

"Fuck yeah," Dean grinned, grabbing the back of Cas's neck to pull him down for a kiss. They both worked their pants off and something dawned on Dean. Sure, he'd been with guys but never all the way.

"I've, uh, never… with a guy, I mean…" Dean stammered, meeting Cas's eyes but looking a little embarrassed.

"Neither have I," Cas said, smiling down at Dean.

"With a girl?" Dean asked. Cas shook his head, now the one to look embarrassed.

"Well, let's make this special, then," Dean grinned, flipping them both over to be on top.


	29. Pancakes

_Pancakes._

That was the first word that came to Dean's mind as he woke up. A lazy smile pulled at his lips as he could smell the pancakes he guessed Sam was making. He was still under his blanket but realized he was cold as he woke up more. His eyes snapped open as he realized what was missing.

_Cas._

Where was Cas? He had spent the night, or most of it, in Dean's arms. Dean still wasn't wearing any clothes after Cas and he…

Dean smiled at that memory. Then panicked. Is that why Cas left?

_Fuck. You took advantage of the guy, he never really had been like that with anyone and you messed it all up. His first time, ruined, and now whatever relationship we had…gone. Fucked up because you couldn't keep it in your pants…_

Dean froze and sat up as he heard laughter. It sounded like Cas and Sam. Dean groaned at the idea of the two of them probably gossiping over breakfast.

_Whatever, _Dean thought, _at least he's still here._

From the floor, Dean grabbed only a pair of sweatpants. The only shirt he found on the floor was one he used to clean himself and Cas up with last night.

Dean sleepily shuffled out of his room. Both Cas and Sam stopped talking and turned to look at him. Cas was sitting at the table with his hair disheveled, probably like Dean's was, in his own pants but Dean's old AC/DC shirt.

"Morning, Cas," Dean grinned and winked, eyeing Cas as he sat down at the table. It looked like Cas wasn't mad at Dean after all, if his blue eyes going over every inch of Dean's bare chest was any indication.

"Hello, Dean," Cas greeted, looking a little sheepish and looking down. Dean loved that Cas could be shy around others when Dean was flirting but when it was just the two of them, he took what he wanted and Dean would never complain about that.

Dean turned to Sam.

"What are you smiling about?" Dean asked, accepting the cup of coffee from his brother and began to take a drink.

"Your brother's happy we had sex last night," Cas stated blatantly.

Dean coughed and sputtered on his coffee, his eyes watering.

"Jesus, Cas…"

"Well, you two weren't exactly quiet," Sam grinned. It was a similar smug smile Cas had seen on Dean. "And it was about time."

"All right, all right," Dean said, grabbing pancakes and hoping to switch the topic to _anything _else. He knew his face was red and Sam's face wasn't helping. "Drop it, Sam."

They ate and talked about trivial stuff like the weather which was fine by Dean. Sam got up and looked into the fridge, seeing something. Or rather, a lack of something.

"Uh, Dean… we don't really have any food."

"So, go get some," Dean said, his eyes on Cas as he bumped their knees together. If Sam left, he could be alone with Cas and talk. He didn't particularly want to but he felt like they should.

"Okay," Sam answered. "How about some money?"

"In my room, my wallet's in my pants. On the floor," Dean said, smirking at Cas.

"Quit bragging," Sam said, rolling his eyes but smiling. He was glad his brother was happy.

"Don't get all healthy shit, Sammy," Dean demanded, turning in his chair at the table to look at Sam who was almost out the door.

"Fine, fine," Sam agreed, leaving and closing the door behind him.

"He's probably still going to get mostly fruit and vegetables," Dean sighed and Cas laughed.

Dean hesitated before getting to a more serious conversation.

"Cas, I…" Dean started, rubbing the back of his neck before he continued, "I thought you left this morning or something, that I messed up again. Taking advantage of you after what happened. I didn't, did I?"

"No, Dean," Cas said, grabbing Dean's hand on top of the table and interlocking their fingers. "You didn't mess up at all, I initiated it, remember? I enjoyed last night. A lot."

Dean smiled, relieved, but was still curious about one thing.

"The nightmare…" Dean started but Cas shook his head.

"I'll tell you about it but not yet. Right now, let's just be happy."

They each took a bite of pancakes with their free hand.

"I do have a question, though," Cas wondered. "Where does that leave us?"

The dreaded question. They'd been on dates and now after last night, what _did_ that make them?

"Uh…" Dean faltered. His normal smooth-talking abilities didn't apply to relationship questions.

"I only ask so we're on the same page, you know? I'm fine with whatever you want," Cas said gently.

"Then…boyfriends?" Dean asked. It was very new area for him and the word felt kind of weird to say.

"I'd like that," Cas smiled, helping to put Dean at ease. Hell, Cas made everything better just by _being_ there and that kind of scared Dean but in a thrilling, new way.

Dean leaned across the table to kiss Cas.

"But, we…um, shouldn't tell everyone. Like the gang, I mean. Only Benny should know, I think."

"Why?" Cas asked, squinting and tilting his head in confusion. Dean took a mental picture because it was still adorable every time Cas did that, even if he would never say that out loud.

"Well, they're not the most open-minded group of guys, Cas. I don't want you to get hurt," Dean explained.

"You don't think I've been called every name in the book for liking guys, too?" Cas asked, still confused and maybe a little upset.

"No, I mean…I _want _everyone to know but… I mean, like last night hurt. I don't want them hurting you. Or anyone hurting you, ever."

Dean smiled and gradually Cas did, too. Dean didn't want Cas to be upset or think he was ashamed at all because he wasn't. Protecting Cas, even though he knew he was capable on his own, had become a priority in his life.

"All right," Cas said, giving in to Dean's sweet talk and kissing him over the table again. Their hands were still tightly wound together on the table.

After Cas and Dean finished eating breakfast and cleaned up, Dean doing the dishes and flicking water at Cas as he dried them, they sat on the couch with the TV on.

Cas looked so cute watching whatever cartoon was on that Dean was going to kiss him when the front door opened and Sam walked in, holding two bags of groceries.

"You better have gotten real food," Dean said, getting up to take a bag. Dean looked up from the bag to Sam's face as Sam shut the door.

"Sammy, what's wrong? You look like you saw a ghost, man," Dean observed, heading to the little kitchen.

"Guess who I ran into at Jewel?" Sam said, almost sounding a little nervous.

"I don't know, Oprah?" Dean guessed with a smirk, setting the bag down.

"You watch Oprah?" Cas chipped in.

"What? No," Dean said, defensively but with a silly smile.

"Lisa. Dean, I saw Lisa," Sam said. That made the smile disappear on Dean's face.

"And?" Dean asked testily. She seemed like a sore subject to bring up from what Cas had noticed.

"She's pregnant."

**AN: For those of you who don't know, Jewel is a grocery store in Iowa/Illinois/Indiana. Thanks!**


	30. Calling Lisa

Dean nearly collapsed at the news that Lisa was pregnant. His mouth fell open and the bag of groceries slipped from his hands on the counter with a crash.

"She…what?" he asked, struggling to find words. The word _pregnant_ was going through his head on a loop, getting louder and louder.

"She's pregnant, Dean," Sam said again, joining Dean in the kitchen area. Castiel stayed rooted to the couch, unsure of what to do.

"I heard you," Dean said, snapping out of it. "Fuck."

He ran a hand through his hair and his eyes stayed glued to the groceries.

"I should… call her? Shit, Sam… how, uh, how pregnant? I mean, like how far along or whatever?"

"Like four months maybe?" Sam asked. Cas figured they'd have to take the word of a sixteen year old boy until Dean did call.

"Fuck," Dean cursed as he did the math in his head, "we broke up…"

"Four months ago," Sam said, confirming Dean's fear.

"Shit," Dean said.

"Weren't you careful?" Sam asked.

"Care- of course we were!" Dean snapped. "I'm not an idiot, Sam!"

"Well, then…"

"I don't know! Just… let me think."

Dean had his hands on the counter for balance, eyes wide with panic. Their break-up didn't end badly, in fact the break-up _sex_ was great. Which was probably exactly how this little problem came to be.

Cas got up and walked next to him. He had no idea if Dean wanted him to say anything or touch him or how to comfort and reassure him. They had only known each other for two months and suddenly that seemed like no time at all.

"I'm sorry, I should go call her," Dean said. He looked up, at Cas, and opened his mouth to speak but shut it again.

He headed into his bedroom and shut the door.

To say that standing there with Sam was uncomfortable was an understatement. Cas said a hasty good bye and headed out the front door. He would just talk to Dean later.

* * *

Castiel had plenty of time to think about the events of last night and this morning as he walked home. Dean was calling Lisa and couldn't drive him and besides, they had left the Impala at Cas's before their amazing second date. Everything was great until Sam came back with the news of a pregnant ex-girlfriend of Dean's.

Cas clenched his fists and realized the thought of Dean having ever been with anyone else, even though he'd seen it before at the Roadhouse, made him angry. And jealous.

His fists unclenched with a small laugh. He was actually jealous. This didn't usually happen. His one brief girlfriend, April, had always thought him devoid of emotion but that couldn't have been farther from the truth. He was just devoid of emotion for _her_.

Dean made him feel all kinds of emotion and the past twelve hours alone had been a roller coaster of them. Joy, hurt, anger, shy, love…

Last night, Dean had been incredibly gentle and loving. Even though they started pretty passionate and rough, he had slowed everything down and made sure Cas was completely comfortable the whole time. Even if neither of them had said it yet, Cas was pretty sure Dean had showed him how much he truly cared with his body and how he looked at Cas's own body and touched him.

Cas smiled with ease as he reached his apartment's building. He knew it didn't matter what the situation was with Lisa or that they had only know each other for two months. Maybe he didn't know how to comfort Dean when he needed it but he would learn.

He loved Dean.

That was clear now. Sure, he wasn't about to tell Dean yet that but he could show him that he cared until they were ready to say it out loud.

**Cas: Call me when you get a chance.**

Cas pressed send as he walked up the stairs. He was still grinning like an idiot as he walked through his front door.

"There he is," Gabriel said with his usual devilish smile from the couch.

"Here I am," Cas agreed, his smile not faltering as he shut the door.

"The hell happened to your face?" Gabriel asked.

"The smile…?" Cas asked. Sure, he didn't smile often but that seemed rude.

"No, dumbass. Your split lip and black eye. Was it this new boy toy of yours? I will kick his ass into next _month_…"

"Gabriel, calm down. It's nothing. And it wasn't my boyfriend," Cas started annoyed but couldn't help smiling again. He had never used the phrase "my boyfriend," he never had one before, and it felt good to call Dean that.

No, it felt _great_.

"All right, little brother, but if you need me to beat up some punks, let me know," Gabriel said, his eyes moving back to the TV but his lips were still pulling up at the corners a little. He was happy his younger brother and the guy who got him flowers were official.

* * *

Dean stood pacing in his room with his phone in his hand. He still had Lisa's number and was hesitating to pressing "call." This was going to be a messy conversation.

_Fuck_, Dean thought,_ everything was going so well…_ Everything with Cas was great and this came along and ruined it. He was pretty sure he heard Cas leave without a goodbye.

"Call her before you walk a hole through the floor, Dean," Sam called from the living room. That was the problem with living in a tiny apartment, you could hear everything. Sam found _that_ out last night.

"Shut up," Dean threw back. He was right, though. Dean took a deep breath and called.

"Hello?" a voice answered after a couple rings.

"Hi, Lisa? It's, uh…"

"Dean, hi," Lisa answered.

"Oh, I…" He didn't know she would have his number still.

"I figured you'd call. Sam talk to you?"

"He did, said he saw you…"

"And he told you that I'm pregnant," Lisa said directly.

"Right to the point, okay," Dean laughed a little, "yeah, that's why I called."

"You don't have to worry, Dean…"

"I'm a little worried," Dean interrupted.

"It's fine, you don't have to worry like you always do. I'll be okay."

"But, I mean… it could be… Couldn't it be mine?" Dean didn't really know what she got up to after they broke up or how quickly, it could be someone else's completely.

"Maybe," Lisa sighed, "that doesn't make it your problem. You didn't ask for this."

"Neither did you," Dean argued.

"What if it's not yours?" Lisa argued back.

"Then I can still be there for you as a friend," Dean said. Their relationship, while it crashed and burned, had been important to Dean and Lisa still was.

"Thank you, Dean," Lisa said, sounding relieved and like she was smiling.

"Let me know if you need anything," Dean said. They said good bye and hung up.


	31. Big News

Castiel didn't expect Dean to call him. He figured he was a little preoccupied with everything that was happening with Lisa. Sure, he _wanted_ him to call, but that was different.

So, when Cas's phone rang and he saw that it was Dean calling, he was more than a little surprised.

"Hello?" Cas answered.

"Hey, Cas," Dean said. Cas could hear him smiling through the phone and he did, too.

"Hello, Dean. How are you?" He would have directly asked about Dean's phone call with Lisa but he figured this would get the conversation there.

"Uh, good, mostly. I talked to Lisa. She told me not to worry…"

"So, of course, you will," Cas said.

"Of course," Dean agreed. One of the things Cas learned right away about Dean Winchester was that he was a protector and always worried about those he felt he needed to protect.

"What are your plans for the day?" Cas asked, changing the subject. Talking about Lisa reminded Cas that Dean hadn't always belonged to him and he didn't like that.

"Work, soon," Dean said. Cas grinned as he pictured him checking his watch.

"Your car is over here," Cas reminded him.

"Shit, I forgot," Dean sighed. "I have an idea! I'll walk over and we'll go together."

"To the garage?" Cas asked.

"Yeah, then, you can meet Bobby!" Dean said, excited.

"I'd like that," Cas smiled, "I'll see you soon."

Dean picked Cas up a half hour later. Cas had showered but put Dean's AC/DC shirt back on because it smelled like him.

"Nice shirt," Dean smirked as Cas got into the Impala.

"Thanks, it's my boyfriend's," Cas smiled and moved closer to Dean to kiss him.

"I'm starting to like that word a lot," Dean smiled against Cas's lips. Cas laughed as Dean started the car and they headed to Bobby's garage. Castiel was starting to like that word a lot, too.

* * *

When they got to the garage, Dean introduced Cas to Bobby who was in his office wearing his usual plaid shirt and baseball hat.

"So this is who got you all worked up for that date a few weeks ago?" Bobby asked, looking at Cas with a sort of amused look. Dean looked down at his shoes. "Kid acted like he'd never been on a date before."

"All right, Bobby…" Dean was red all the way to the tips of his ears and rubbed the back of his neck. Cas put all of his effort in not laughing for Dean's sake.

"It's my job to embarrass you, you know that. Now, those cars aren't going to fix themselves," Bobby answered.

"Got it," Dean said, relieved to leave before Bobby said anything else embarrassing.

"Nice to meet you, Bobby," Cas said as Dean practically dragged him out of the office.

"You too, Cas," Bobby called as they exited.

Dean quickly turned to the radio to get something playing to distract him. He could feel Cas's eyes on his back.

"Stop that," Dean said, popping in a AC/DC cassette.

"Stop what?" Cas asked with mock innocence.

Dean hit play and turned around. Cas was leaning against the first car he was going to work on with his arms crossed.

"No staring," Dean said, walking over to stand right in front of Cas. He didn't actually mind the way Cas looked at him or how often but he wasn't going to say that to him.

"Can't help it, you're kind of attractive," Cas said with a small smile, his eyes flicking down to Dean's lips briefly.

"You're not too bad yourself, Cas," Dean said before kissing Cas. He leaned into him, pressing Cas's back against the side of the car. One of Dean's hands was on the back of Cas's neck, teasing at his hair and the other was on his waist. Just as he was sliding his hand under Cas's shirt, Bobby's voice called out from his office.

"That's not what I pay those hands to do. Get to work, boy," came the good-natured call.

"Yes, sir," Dean answered. He reluctantly let go of Cas and backed up a step, his face red.

They spent the next few hours at the garage. Dean worked and talked to Cas as they enjoyed the music and each other's company.

When Dean was done for the day, the two of them said bye to Bobby and walked outside. Benny was waiting for them next to Dean's car.

"Hey, Benny," Dean greeted. He didn't seem shocked to see Benny and Cas guessed he showed up here a lot.

"Hey, guys. I have some news, can we go to the Roadhouse?" Benny asked.

Dean and Cas looked at each other and shrugged. It was about time Cas smoothed things over with Jo. He only met her twice but didn't care to have her as an enemy or even just mad.

The three of them got into the car and headed to the Roadhouse.

"I didn't know you liked AC/DC, Cas," Benny observed from the backseat.

"I… oh, the shirt. It's actually Dean's," Cas grinned.

"Oh…_oh,_" Benny said, putting two and two together before he laughed. Cas and Dean glanced at each other before joining.

* * *

Once at the Roadhouse, Cas immediately went to the bar to talk to Jo.

"Hello, Jo," he greeted.

"Cas," Jo said shortly, focused on the drinks she was pouring.

"I wanted to apologize again…"

"No need to apologize," Jo said with a sincere smile. "I knew he never liked me like that, I was just too stubborn to see it. Just take care of him, okay?" Jo was being a lot more understanding than Cas expected.

"I will," Cas said. He headed back to Dean and Benny.

"Okay, what's this news?" Dean demanded. Cas was pretty curious himself.

"Andrea and I are engaged," Benny announced with a proud smile.

"Really?" Dean asked, dumbfounded. Cas was equally shocked. For a couple that seemed to fight a considerable amount, this seemed like a huge step.

"Yes. And we want it to be pretty small, probably the first weekend in October."

"That's…soon," Cas pointed out.

"Yeah, well… Guys in our line of work don't have much in the way of a lifespan. Figured, life's short, why not?" Benny explained. "Dean, I gotta ask…"

"What is it, Benny?"

"Will you be my best man?"

"Of course!" Dean exclaimed.

"Thanks, brother. And Cas, you'll be a groomsman, right?"

"Sure, Benny," Cas agreed.

"I've actually got news for you to," Dean said, hands playing with the paper around his beer bottle.

"What's that?"

"Remember Lisa?"

"Yeah, what about her?"

"She's pregnant."

"Shit!" Benny said rather loudly, turning a couple heads in the bar. "Is it yours?" he continued, in a softer voice.

"No idea, I just told her I'm here for her for whatever."

"Wow."

"Sums it up," Dean agreed. "When did we get so fucking _old_?"

"I don't know, man," Benny shrugged. The three of them laughed and ate their burgers when they showed up.


	32. Turning Tides

_The three of them laughed and ate their burgers when they showed up._

"They" unfortunately meant Azazel and Alastair who were accompanied by Crowley. Castiel's stomach dropped but he tried to keep a straight face. Dean gave his hand a squeeze under the table before letting go.

"We're figured we'd find you here," Alastair said, creepy as usual. One look from Crowley and he shut up and looked at the ground.

"I see my boys did quite a number to your face, Cas," Crowley said, more smug than he normally seemed.

"That's bound to happen, seeing as it was two on one," Cas said, casually eating a fry. Dean glanced at Cas with a smile before turning back to Crowley. He loved when Cas was a badass, plain and simple. He nudged Cas's knee under the table in silent support.

"See, it's not supposed to happen. They did it because they are under the impression that you are snitching to the cops," Crowley responded, his two attack dogs still obediently quiet at his side.

"Cas would never…" Dean started to defend Cas but was interrupted by Crowley.

"Watch it, Winchester, you're on thin ice considering _you_ are the one who's been bringing him around," he jabbed before turning back to Cas. "If you _are _a snitch…?"

Crowley trailed off which was scarier than if he hadn't.

"Let's hope for your sake," his eyes went to Dean, "both of you," his eyes flicked back to Cas, "you're not. These two don't play nice." He gestured to Alastair and Azazel.

Before Crowley left the bar, he shifted his eyes one more time between Cas and Dean and seemed to nod subtly. Nod like he knew something or figured something out. He smiled evilly without showing any teeth and finally left.

Cas was terrified.

Dean gave his hand another squeeze under the table that helped a little but Dean's eyes gave away how he felt.

He saw the same thing and was just as scared.

* * *

July melted into August and Cas spent more and more nights at Dean's. They both continued to work and sell on their corner. Benny wasn't around as much because he had a lot of planning to do for the wedding and according to him, he and Andrea and a lot of different ideas they were working out. There was nothing new with Lisa and her pregnancy and Sam continued to hang out with Jess as much as he could. Crowley, if he was still worried about Cas being a snitch, hadn't said anything.

On the first Saturday of the month, Cas decided he was going to treat Dean to a surprise date like he did for him. It was a ridiculously hot day and Cas decided a trip to the beach would be a good idea.

**Cas: Are you home?**

**Dean: Yeah, y?**

**Cas: Let me in, I'm outside.**

Cas patiently waited outside of the apartment building until Dean came outside with a huge smile on his face.

"To do what do I owe the pleasure?" Dean asked.

Cas kissed him before he answered.

"I'm taking you on a date," Cas said, arms still around Dean.

"Really? Where to?"

"The beach," Cas said.

"Aw, you ruined the surprise!" Dean said, pretending to pout.

"I told you, I don't like surprises."

"Yeah, but I do!"

"Then you shouldn't have asked."

Dean laughed. "Fair point. Let me get changed."

After Dean ran upstairs to change, he drove them both to a beach on Lake Michigan.

They set up their towels and headed to the water's edge where they found out that it was freezing. Their feet were in barely in an inch of the water.

"Nope, too cold," Dean said and started to back up. Cas grabbed his hand to stop him.

"It is not, don't be a baby," Cas said, pulling him back into the water.

Dean narrowed his eyes. Cas figured that would be the way to get him worked up and to get him to come in the water.

"Fine," Dean said. He began to walk into the water, pulling Cas with him.

They got knee deep and had to stop because it was too much.

"All right, hold on," Cas stopped them.

"Now who's the baby?" Dean teased. Cas dropped Dean's hand. "What?" Dean asked.

"I dare you to go underwater."

"I dare _you_ to go underwater," Dean responded.

"I said it first," Cas retorted. Dean's answer was to pull Cas into a kiss instead.

"You're cute when you're demanding," Dean said. Cas smiled. He was going to answer but before he could, Dean tackled Cas under the water.

Cas came up sputtering and Dean was laughing.

"You… you ASS!" Cas cursed.

Dean was laughing too hard to say anything to that. Castiel couldn't stay mad at Dean for long and cracked up too.

"Let's get out of the water, it's freezing!" Dean said and Cas agreed. As they walked out of the water, Cas pushed Dean over into the water.

As Dean stood back up, he was still grinning like crazy.

"All right, truce!" he called.

They walked hand in hand back to their towels and ate the sandwiches Cas made and brought with.

"You know the way to a guy's heart, Cas," Dean said, taking a bite.

"I've heard it's through his stomach, yes," Cas said, biting his own sandwich.

"This was a great idea, Cas. You're the best," Dean said, still focusing on his sandwich.

"Thanks," Cas smiled.

* * *

The first week of August was more of the same until Henriksen and Mills called Cas into the station. He was with Dean but had to make up an excuse to leave even though that was the last thing he wanted to do. Lying to Dean was terrible but he just had to find a way to figure this all out. He needed more time.

Cas sat down at the table across from the officers.

"What's up, guys?" Castiel asked.

"We need to know where their product comes from. The big picture," Henriksen said.

Cas nodded.

"How is everything going with those guys?" Mills asked.

"Um, good, mostly. Well, except when two of them beat me up because they think I'm working for the cops."

"You are," Henriksen observed.

Cas shot him a bitchface Sam would be proud of.

"Obviously but I'd prefer they didn't know that, though. How can we fix that?"

"We could arrest you in front of them, would that help?" Mills suggested. Cas thought it over and nodded.

"All right, we'll set something up. Keep us updated to anything, drag racing or parties or whatever they get up to, okay?" Henriksen said. Cas nodded and Henriksen left the room.

Mills was about to follow him when Cas stood up and stopped her.

"Officer Mills…"

"Jody," she insisted.

"Jody, I have a question. Is there any possibility Dean gets left out of all of this?" Cas asked.

"We only have proof from you that he sold to you once. If he gets out now, there is a possibility."

"Thank you," Cas said, grateful. Jody smiled knowingly. If there was any chance he could hide how he felt about Dean from her, it was gone now but Cas didn't care.


	33. Cas's Music

The Saturday before Sam had to go back to school, Dean was working when he got a text from Cas that said he should come over. Dean almost threw down his tools and ran out of the garage then and there but texted back he would have to wait until work was over. Unfortunately.

Those hours dragged until Dean could finally leave. He tried to focus on the cars and his music but thoughts of Cas kept interrupting. It normally would have been a welcome distraction but not when he was so close to seeing the real deal.

"See ya, Bobby!" Dean said at two, sticking his head in the office briefly with a huge grin.

"Going to see this boyfriend of yours?" Bobby asked, a sly smile barely pulling at his lips.

"That obvious?" Dean responded, smiling bigger.

Bobby nodded and Dean laughed before dashing out to his Impala and flooring it to Cas's. It was a miracle he didn't get pulled over.

At the front door, he got buzzed in and ran up to see the front door to Cas's apartment was open. Dean walked in semi-cautiously, always prepared for the worst. His hand went immediately to the back of his jeans were his gun always was.

"Cas?" Dean called, worried.

"In here," Cas's voice rang out from his bedroom. Dean immediately had all kinds of ideas that he quickly shut down. For now.

"Hey Cas," Dean greeted, relieved to see Castiel relaxing on his bed.

"Hello, Dean. I missed you," Cas said with a smile, not getting off his bed.

"You saw me yesterday," Dean retorted. He kicked his boots off and joined Cas on his bed, giving him a quick kiss. Cas had one earbud in. Dean laid down on his side, facing Cas.

"So? I still missed you, you smartass."

Dean laughed. "I missed you, too. What are you listening to?"

Dean put the other earbud in. It was classical music.

"What is this?" Dean asked, biting the inside of his cheek to not laugh. He hated when anyone made fun of what he listened to, mostly Sam, and he didn't want to be hypocritical.

"Classical music. I find it relaxing," Cas said, closing his eyes.

Dean had to agree, it was nice. He picked up Cas's iPod and scrolled through the songs. Besides the classical music, there was a lot of stuff he liked, too.

"Cas…"

"Yes, Dean?" Cas opened his eyes.

"You have AC/DC, Led Zeppelin…" Dean kept scrolling, finding many surprises among the Beethoven and Mozart. "Journey? Metallica?"

"I might have gotten those after being in your car and hanging out with you," Cas said, looking a little sheepish.

"So, I'm a good influence," Dean smirked. Cas rolled his eyes with a smile.

Dean put on "Faithfully" by Journey and Cas laughed.

"What's so funny?" Dean demanded, although he didn't mind. He could listen to Cas laugh anytime.

"Do you know why I have this song?" Cas asked.

"It was on the radio first night you were in my car. Sam and I argued about leaving it on," Dean grinned, recalling that night well.

"Exactly. You're such a sap but I love that you remember," Cas said, grabbing one of Dean's hands. It was dangerously close to "I love you" but still carried a similar sentiment.

"You remembered, too. Enough to put it on your iPod so we're both saps," Dean pointed out.

"Smart ass," Cas said again, kissing Dean.

"Knew I liked this song," Dean smiled against Cas's lips, resting their foreheads together. Cas casually ran his thumb of his free hand over Dean's necklace.

"You always wear this," Cas observed, eyes on the necklace. It was also an invitation to talk if Dean wanted to. The hand not holding Cas's reached up to cover his hand around the necklace.

"Sammy gave it to me when we were little, for Christmas. It was going to be for our dad, I think, but he never showed," Dean laughed bitterly, one short bark that worried Cas.

"Did you want to…"

"Nah, it's all right. The past is the past, you know?" Dean said, a small, sad smile not quite lighting his eyes the way Cas loved.

They remained quiet, simply holding hands, as the iPod switched to another classical song Dean didn't recognize but liked right away. It had a calm beginning but with a powerful background that would occasionally surge through to the front and was consuming.

As that song ended, Dean brought up something he had been meaning to for a while.

"Cas, when are you going to tell me about…"

"My nightmares?" Cas asked with raised eyebrows.

Dean nodded, still amazed at how easily Cas could read him when he didn't finish saying what he meant to.

"They used to be worse," Cas started, taking a deep breath before he continued, "Used to be every night. Now, I'm lucky, maybe once a week? Sometimes less. And they're not terrible, I just wake up, panicked, then fall back asleep. They actually stopped for a while when I met you," Cas smiled, glad he was finally telling Dean that. He didn't know why he didn't earlier because it made Dean smile, ear to ear.

"Really?" Dean asked, genuinely glad he had a legitimately positive effect on Cas besides adding good music to his library.

"Yeah, until…" Cas trailed off.

"Until I brought up shitty days," Dean cringed. "I'm still sorry about that, you know."

"I do."

"Do you want to talk about it?" Dean asked, not one for these heart-to-hearts, but if Cas needed to talk, he was here. And he genuinely cared, he wasn't just saying it to get in his pants. Mostly because he already did but also because this was different. _Cas_ was different. It was really the only time he and been in someone else's bed with _clothes_ on.

"Not much to tell. I mean, shitty foster homes and juvie? You see stuff, stuff happens to you. People hate you, beat you… Those you care about. And I really should have learned to not mention being bi," Cas explained. He could feel Dean's hands clutch tighter around his.

"Those fuckers…" Dean growled, a low voice that got Cas a little excited despite the situation.

"I've left it all behind, Dean. And I'm stronger because of it," Cas said, a hand caressing his cheek. "Although this protective side of you is hot."

Dean laughed and Cas could feel the tension leave his body.

"_Every_ side of you is hot, Cas," Dean said, a glint in his eyes as they moved over Cas's body.

"Always have to one up me, huh?" Cas asked, pressing their lips together.

"Why, yes I do," Dean said, returning the kiss and rolling on top of Cas. So much for staying clothed.

Castiel could let Dean one up him. This time.

**AN: Thanks for reading! **


	34. Crash

When Castiel and Dean had finished and cleaned up, they continued to lie together in Cas's bed without clothes or the music from before.

Dean untangled himself from Cas to grab his phone from his jeans on the floor.

"Fuck, it's already five," Dean cursed. Cas furrowed his eyebrows.

"Do you have to go somewhere?" Cas asked, doing his best to use a low, sexy voice to keep Dean from leaving.

"No," Dean said, distracted by Cas's voice, "Yes. Damn. I'm supposed to be selling with Benny."

"Tell him to sell without you," Cas said. Anything to get him to stop selling and hopefully stay off of Mills' and Henriksen's radars.

"I… Actually, one time wouldn't hurt. Benny's a big boy," Dean grinned, tapping out a text to Benny and throwing his phone on the floor.

"So, you'll stay?" Cas asked, pleading more than he had meant to.

"I'll stay," Dean said. He climbed back next to Cas, kissing him before pulling him against his chest.

Benny stood on the usual corner, laughing softly as he checked his phone.

**Dean: Sell w/out me, with Cas. ;)**

Benny didn't bother with a response because he figured Dean was otherwise engaged. He sold and smoked a few cigarettes for about an hour before Crowley showed up with Alastair.

"Benny," Crowley said. Benny nodded in greeting.

"To what do I owe the pleasure, Crowley?" Benny asked, stepping out his cigarette.

"Where's Dean?" Crowley asked, always one to get right down to business.

"In the store," Benny said, "Needed snacks."

Crowley ignored the joke and looked at Alastair, jerking his head towards the store. Alastair gave Benny a smug sneer before walking into the store. Benny calmly lit another cigarette as he waited for his story to fall apart.

Alastair came back out and shook his head.

"Benny, come on. Don't lie to me," Crowley drawled. As little as Crowley scared Benny, two on one odds in a fight were never good. "Where is he?"

"Sick. But he didn't want me to tell you. Couldn't appear weak," Benny lied, puffing on his smoke.

"He's with Castiel, isn't he?" Crowley asked. Benny said nothing. Crowley nodded, seeming to take the silence as a yes.

"Let Dean know we stopped by, will you?"

With one last smug grin from the pair, they left Benny alone.

When Dean finally decided he should head home because he promised Sam a movie night, it was dark. There were a couple texts from Benny that Dean figured he could read later. Cas and his lips were saying a very heated goodbye.

"Can I see you tomorrow?" Dean asked.

"When I'm not working, sure," Cas answered, kissing him again.

Reluctantly, Dean left. When he got home, he quickly apologized for staying a little later at Cas's than he meant to. Sam understood and gave him silly grin.

"Shut up and pick a movie," Dean said, heading to the kitchen to make popcorn. When it was made and the movie, _The Breakfast Club_, was on, Dean finally checked Benny's messages.

**Benny: That's fine, brother. Have fun **

**Benny: Crowley was here, figured u were w/ Cas. not good**

Dean's stomach dropped. This wasn't good in any way, shape or form.

"What's wrong?" Sam asked, sensing the tension.

"Nothing I can't handle, just a little trouble with Crowley," Dean said, more honest than usual. He put his phone on the coffee table and kicked his feet up as well.

"Who's Crowley?" Sam asked, confused.

"No one. Watch the movie, it's your pick."

"Whatever. Your shirt's inside out by the way," Sam smirked, reveling in this small victory.

"Son of a bitch," Dean said, standing up to fix it. Sam was cracking up as Dean sat back down, warranting Dean to throw popcorn at him before he picked up his phone.

**Dean: You didn't tell me my shirt was inside out!**

**Cas: It was too cute.**

**Dean: That falls under 'boyfriend duties' just FYI**

**Cas: Duly noted, boyfriend.**

**Dean: ;)**

"Texting Cas?" Sam asked, looking bemused.

"Yeah. How…?"

Sam just raised his eyebrows and Dean shrugged.

"Shut up," Dean said with a smile. Texting Cas was always enough to put him in a great mood. Especially if he called him cute. And boyfriend. Dean smiled down at his phone, missing Cas.

"So, how's Jess?" Dean asked, changing the subject.

"Great! Really great. I'm excited for school to start," Sam said. Dean rolled his eyes good-naturedly and it was Sam's turn to throw popcorn at him. "I am! We have some classes together and lunch. And I can see her a lot and we can let everyone know we're dating."

"Who knew you were such a romantic, Sammy," Dean teased.

"Says the guy who brought flowers for the first date," Sam teased back, drinking his Coke.

Dean turned red and drank his beer, not responding. It was true, after all.

"Would you say," Dean paused, serious now, "would you say you love her?"

Sam slightly sputtered on his Coke, coughing a little.

"Maybe? I don't know. I know I like her a lot and always want to be with her. When something happens, even something little, I want her to be there to share it with me."

"I think you might love her," Dean said, slightly shocked at how mature his sixteen year old brother was.

"Are you basing this off of how you feel about Cas?" Sam asked.

"I… I guess. I mean, I feel what you described but… I've never said it. To anyone."

"Not even to Lisa?"

Dean shook his head. It had really been more physical of a relationship than anything else.

"Wow. So, you think you love him. But you're too scared to tell him?" Sam summed up.

"Yeah," Dean admitted, embarrassed at how much of a chickenshit he was being. It wasn't like him to be scared. Ever. But Cas came into his life and changed everything. Before Cas, Dean didn't stay to cuddle or really do relationships besides his one with Lisa. Cas met his family, knew him probably as well as Sam, if not better sometimes. And sleeping with him was special, it was intimate and meant something.

It was love, wasn't it? Dean didn't have much to compare it to.

How was Dean going to admit to Cas he loved him when he could barely admit it to himself?


	35. Ruby

Crowley had it on good authority that Benny sold without Dean again the following Saturday, the authority being the only one he trusted. Himself.

There had to be a delicate way to go about this, Crowley figured. Castiel had proven useful but the accusations of him being a narc had to be checked out immediately. Crowley didn't want to get rid of Cas if he could use him but only if he wasn't a threat. Threats had to be eliminated.

But he also needed Dean.

Dean was his right hand man, normally. A great seller, fighter, racer… He was important to this gang and Crowley would be damned to let him go that easily and lose him to a boyfriend of all things. In Crowley's mind, love of any kind was stupid and a waste of time; guys, girls, didn't matter. It never made sense to him. Business, he could handle. Deals, he understood.

Besides Cas, there was something, or someone, that could get Dean to do what Crowley wanted. The same way Crowley got Dean in the first place.

This Saturday night was another party at Crowley's. Benny had arrived with Andrea and Dean and Cas were nowhere to be seen. Crowley didn't bother talking to Benny because if Dean wasn't with Benny there was only person he could be with.

On the couch, Meg and Ruby sat next to Crowley on either side.

"Ruby, the high school is back in session, correct?" Crowley asked. He was sipping scotch, his usual. He didn't understand the love people there had for fruity mixed drinks with cheap vodka.

"Yeah, why? Are we recruiting? I think I heard Michael's been trying to."

"And you failed to mention that?" Crowley glared. Meg snickered, earning a glare as well. If Michael was stooping low enough to search for members in the high school, he would have to as well, at some point.

_We could pretend to have standards but desperate times, blah blah blah_, Crowley thought.

"They've been back for half a week!" Ruby argued defensively.

"Never mind," Crowley waved her off. He could deal with Michael later. "I do need you to recruit, actually. There's one specific person from that high school I want. And you're going to get him."

"Who?" Ruby asked, always up for a challenge.

"Sam Winchester."

* * *

Besides Sam having started school, Castiel and Dean followed through on their idea to get their GED's. Their classes were a few nights a week and it was a pretty big change for them because neither of them had been to school in a few years. Both of their jobs had been flexible when needed but it didn't really prove to be a conflict for either of them.

Dean would have stopped going completely if it wasn't for Cas's support and encouragement. This wasn't easy for Dean the first time and it wasn't easier now. But Cas made sure all of the homework got done and that they studied for every test.

The teacher, Pamela Barnes, was tough but fair. She always knew when Dean and Cas were talking, goofing around or otherwise not paying attention in the back of the room and would call them out on it every time.

"This doesn't make sense. I hate math," Dean said, dramatically dropping his pencil and flopping his head on the table in his apartment. He forgot how shitty he was at algebra. Or math of any kind.

"Come on, you can do this, Dean, you know you can," Cas said. He picked up Dean's pencil and handed it him. This had all come back fairly quickly to Cas who maybe just had been trying harder. "You know you're smart, right?" Cas said, trying to reassure Dean.

"This was a bad idea," Dean grumbled as he retried the problem in front of him, ignoring Cas's compliment.

"It was _your_ idea, babe," Cas said, turning red immediately after he said it.

Dean simply raised his eyebrows at him, a smile pulling at his lips.

"Now, how am I supposed to study with you saying such things and being all cute?" Dean grinned fully as he enjoyed Cas stay flustered. Getting Cas worked up and squirming was something Dean would much rather be doing.

"Whatever, just keep working," Cas mumbled, looking down. Dean grabbed his hand across his table and waited until Cas met his eyes.

"All right," Dean winked, "_babe_."

Cas laughed. "Asshole."

* * *

Sam walked out of school at the end of the day the following Wednesday with Jess. They were holding hands and he walked her out to where her mom was parked to pick her up. Sam gave Jess just a hug goodbye and waved at Ms. Moore.

As he went back to a bench next to the school's front doors to wait for Dean to pick him up, a dark haired girl he had never seen before walked up to him. She was smoking a cigarette.

"You smoke?" she asked, sitting next to Sam on the bench.

"No," Sam said, wrinkling his nose. He hated when Dean smelled like it and never wanted to try. She shrugged.

"Name's Ruby," she said.

"Sam," Sam answered. Ruby nodded. "I've never seen you around, Ruby."

"I don't go here. I did a couple years ago."

"You graduate?"

"No," Ruby said, not giving any other explanation. Sam raised his eyebrows.

"So, what are you doing here?"

"I was walking by and you seemed… interesting. Wanted to say hi."

Sam laughed as Dean drove up. He wasn't really used to a stranger striking up a conversation with him so casually.

Sam walked towards the car after saying a brief goodbye and Ruby stayed on the bench.

Dean parked and was walking towards Sam.

"Dean, what…"

"Sam, get in the car."

"Dean…" Sam said, confused.

"Car," Dean growled and Sam listened. From the car, Sam watched Dean walk over to Ruby and was dying to know what they were saying.

"What the fuck are you doing?" Dean demanded as Ruby stomped out her cigarette.

"I'm sitting," Ruby said.

"Look, I don't know what you and Crowley are trying here but it stops. Now. You leave Sam out of this, all of this, got it? I joined so he would never have to. He's off limits and Crowley knows that."

"Tell him yourself," Ruby paused, "Oh that's right… you're never around anymore."

"Just fuck off, okay?" Dean said and headed to the Impala.

"How do you know her?" Sam asked when Dean got in, curious as hell.

"I don't," Dean snapped.

"Come on…"

"Drop it," Dean said, pulling out onto the street. "And stay away from her, you hear me?"

Sam didn't answer.


	36. Highway to Hell

Of course, Dean telling Sam to _not_ talk to Ruby only made him want to talk her more. He regularly looked for her after school and he wasn't sure why. Jess was still very much a part of his life and he would walk her to her mom's car then look around for Ruby. He couldn't explain it but she was oddly magnetic.

One early September day after school, Sam had to walk home because Dean was working at the garage. Ruby was standing on the sidewalk, technically off of school property because she was warned by the principal to stay away. That principal didn't have fond memories of her attendance there. She was facing away from the school, smoking a cigarette.

"Hi, Ruby," Sam greeted.

"Hey, Sam," Ruby smiled as she turned around. They began to walk towards Sam's apartment.

"So, if you went here, what do you do now? School?" Sam asked, genuinely curious about the enigma that was Ruby. Hell, he didn't even know her last name. He felt his phone buzz in his pocket but he ignored it.

"Nope," Ruby said, hip bumping Sam as they walked.

"Work?" Sam guessed.

"Sort of," Ruby said, pleased to see Sam getting a little frustrated.

"Fine, don't tell me anything. I won't tell you anything, either," Sam teased.

"Well, we're walking to where you live, I assume, and I know what your girlfriend looks like even if I don't know her name. And I know your brother."

"How _do_ you know my brother?" Sam asked, still ready to give up almost anything to know.

"Oh, Dean and I go way back. But that's his story to tell."

They continued to talk until they reached Sam's building.

"See ya around, Ruby," Sam said.

"Sure," Ruby said. Sam turned to head into the building. "Oh, and one more thing, Sam," she called. Sam turned back around.

"What?" Sam asked as Ruby handed him a piece of paper.

"Here's my number," she said and with a wink, she left.

Upstairs, Sam checked his phone.

**Jess: You didn't wait after school, everything ok?**

Sam, who had waited long enough to answer her, replied after an inward cringe. How could he be so stupid?

**Sam: Sorry, I'm fine. Just had a lot on my mind I guess. I'll see you tmo.**

**Jess: All right.**

Sam knew the period at the end of a two word response was never good. Tomorrow, he would have to face an angry Jessica and hope they could smooth this over and avoid their first fight.

"Dean, what's going on?" Cas asked. It was a few days after Ruby walked Sam home, which Dean still didn't know about. They were in Dean's bed and Dean seemed jittery instead of tired like he usually was after they had sex. They had taken advantage of having an empty apartment.

"Nothing," Dean lied.

"Right," Cas rolled his eyes. "Just tell me."

"Fine," Dean sighed, "I'm a little freaked because Crowley, who's pissed at me, and Benny are coming to get me soon and I have to go help get a new shipment."

"Of weed," Cas said, knowing full well that was what Dean meant. Dean had also explained already the trouble brewing with Crowley and his supposed lack of devotion to the gang.

"No, copies of _Harry Potter_," Dean said with his own eye roll.

"You don't have to be a dick," Cas responded.

"Come on, you love it," Dean said, snuggling against Cas's side.

"You being a dick? Not really," Cas said honestly.

"When am I ever a dick?" Dean asked, propping himself on one elbow to look at Castiel.

"Right when I met you?"

"I was not!" Dean protested. Cas just tilted his head and raised his eyebrows in a "Really?" gesture.

"Fine," Dean admitted. "When else?"

"The Roadhouse when you got shitfaced?" Cas continued.

"All right, I get it," Dean grinned, leaning over to kiss Cas. "But I'm a lovable dick, right?"

Cas's stomach flipped at the "L" word, still close but not actually saying it, either of them. He wondered how long they could dance around it. Cas nodded with a smile and kissed Dean back as a response.

They both got dressed and walked out to the front of the apartment building. Cas was going to wait until Benny and Crowley showed up to pick Dean up then head home.

When the car pulled up on the side of the street, Crowley driving, both Dean and Cas stood.

"Castiel, good, I figured you'd be here," Crowley said with only a slight sneer. "Get in," he demanded, leaning over Benny in the passenger seat to instruct them.

"What? No, you…" Dean attempted, trying to keep Castiel out of whatever Crowley had planned. Dean knew he was pissed at him and didn't know how far he was willing to go. The entire gang except Benny would be on Crowley's side if this went south on the two of them and Dean wanted Cas as far from that as possible.

"Shut up and get in. I won't ask again," Crowley threatened. They both got in.

Cas and Dean nervously sat side by side in the backseat of the car. As much as Cas wanted to reach out and grab Dean's hand, he figured this would be the worst place for it so he kept them folded in his lap. Dean was doing the same thing and Cas could only guess it was for the same reason.

Right now would be a perfect time to text Mills and let her know what was going on. It was a great opportunity to prove he wasn't a narc or at least pretend he wasn't and extend the charade. Crowley, however, continuously checked the rearview mirror to look at Dean and Cas.

Cas, despite the severity of the situation, bit his tongue to hold in a laugh. They had arrived at an abandoned warehouse that screamed cliché. He looked at Dean, who smiled, and knew he was thinking the same thing. It made him feel much better.

Castiel wasn't sure what Crowley's plan was but he was guessing they were going to find out.

Once inside the warehouse, Castiel found that the rest of the gang had assembled already.

"Dean, almost forgot who you were," Dick said with a wicked, partial smile. That got a few laughs from the gang.

"I can still take any of you assholes in a fight or a race so shut the fuck up," Dean said forcefully.

"What about Cas here? Think you can take any one of us in a fight?" Edgar jeered.

"No," Cas said, then smirked, "I _know_ I can."

Edgar surged forward angrily to test that but was held back by Dick and Alastair. Cas had taken a single step forward, ready to take Edgar on, and Dean had protectively stepped in front of him, extending an arm across his chest to stop him. The slightly confused glances from the guys weren't as concerning as what Crowley was planning. They could think what they wanted about Cas and Dean, it wouldn't matter if Crowley got too drastic.

"Everyone cool down," Crowley's voice cut sharply across the warehouse. Edgar stood up straight, not planning on charging anytime soon, but kept glaring at Cas.

"Product should be here soon," Crowley informed them.

**AN: Here's some thanks to reviewers. Also, as an FYI I added my tumblr on my profile page here if you're into that kind of thing.**

**Dancerline: Thanks for all your support!**

**ciprianoivashkov: Your many reviews inspire me and I like them a lot!**

**cherrytops82: Thanks for the encouragement as always.**

**lindsayd16: Your review actually helped me with an idea so thank you a bunch!**

**lookingforsomeDestiel: Welcome to the party!**


	37. Don't Fear the Reaper

**AN: Sorry for the slight delay but here it is, enjoy! Also, I've been loving your reviews, they keep me going so thanks!**

Crowley tried to gather the group in a circle as they waited for the product to arrive despite the tension splitting them in half. He told them that the weed would be hidden inside something but even he didn't know what. There was still a ridiculous amount of tension between the two sides in the warehouse. Dean, who had stepped back next to Cas, and Benny were one side, backs to the front doors, and Alastair, Azazel, Jake, Gordon, Dick and Edgar were facing them. Crowley stood, seemingly neutrally, in between them with each group to one side of him.

They were in what resembled a clearing in a forest between old boxes and crates of stuff from when the warehouse was used. It was almost a maze, one Cas was all too eager to escape.

Cas knew that Crowley wouldn't hesitate to back the other side over their little group of three and the false neutral wouldn't last if a fight broke out. Plus, Cas assumed they all had guns which he did not. He didn't care for them and found them useless. Guns only brought death and pain.

"Well, isn't this a cute little group," came a voice from behind Dean, Cas and Benny who turned around. They weren't keen on having their backs turned to the guys who would as easily stab them as they would breathe but there wasn't a choice. The big, bad supplier was here and the focus had to be on him.

"Lucifer," Crowley said, extending a hand to the newest addition into the shady warehouse. Cas detected a little bit of wary hesitation, almost like Crowley was scared of the cool, almost bored looking blonde man. Dean and Benny tensed as they shook hands and Cas guessed the rest of the gang behind them did, too. This man exuded a power and confidence that instilled fear.

Lucifer's eyes scanned the group and stopped on Castiel.

"Oh, you must be new," he observed.

"_You_ must have been top of your class, very smart," Cas retorted, sounding braver than he felt. Lucifer eyed him with new amusement which Cas figured was a bad thing. Castiel could tell Dean was trying hard not to laugh, Cas's witty rejoinders cracked him up.

"Aren't you peculiar? People don't normally talk to me like that," Lucifer said, even and calm but with an undertone of authority. He sauntered a few steps until he was standing directly in front of Cas. Cas could feel Dean on his right ready to jump in front of him and fight this guy which was comforting but unnecessary. Castiel could handle himself and Dean knew that but that went both ways. Cas wanted to protect Dean from Crowley and now this new douchebag even though Dean could handle himself just fine.

Cas just shrugged in response to Lucifer's comment. He could feel Crowley's eyes glaring a hole through his skull from his left side. Disrespect wasn't taken lightly by guys like Lucifer, especially in this line of work.

"Funny, I would have pegged you for the other group," Lucifer said, still looking at Cas with interest and curiosity, almost like he was solving a puzzle.

"What are you talking about?" Dean demanded to know as Cas tilted his head to the side and squinted in confusion. He also wanted to know what Lucifer meant. Did he mean the other gang?

"Winchester, right?" Lucifer commented, sliding his eyes over to meet Dean's, "Heard a lot about you from Crowley."

"Yeah, like what?" Dean snapped. He knew of Lucifer from Crowley but he didn't like that they had been swapping stories.

"For one, your lack of respect for those above you," Lucifer said. Dean set his mouth in a hard line. His teachers in school always told him he'd end up saying the wrong thing to the wrong person. This might have finally been what they were talking about.

"And how you make stupid decisions to protect those you love," Lucifer said, his eyes flicking to Cas briefly before returning to Dean with a small smile that terrified Castiel. Dean and Cas were both at a loss for words. Crowley must have mentioned Dean joining the gang to protect his brother but he hoped he didn't mention his theory about Dean and Cas dating. Despite being true, the two would have preferred that people like Lucifer didn't know. It was ammo in a very dangerous gun.

"Are we going to do this or what?" Crowley said, growing impatient.

"Not yet, we're waiting for something," Lucifer said. One look had Crowley standing up straighter and remembering his place.

"Waiting for what?" Crowley asked, curbing his attitude. For the one usually in power, he was clearly not sure how to handle being the subordinate.

"What the hell is this?" asked the guy who just walked in through the warehouse's doors leading his own gang.

It was Michael.

"For that," Lucifer said with a malicious smile before making a beeline into the maze that was this warehouse.

Before Cas could blink, he was being pulled down to the ground and to the side by Dean. They crawled on the dusty concrete floor behind stacks of cardboard boxes, old plastic crates and whatever else was piled up to avoid the gunfire that had started. Dean pulled his own gun from the back of his jeans and began to return fire in the direction of Michael's gang. It started so fast, Cas really only saw Michael and didn't know how many guys he had brought with him.

Someone was laughing, presumably Lucifer, as the gunfire rang and echoed. Cas couldn't think and was too shocked and petrified to move. Dean was trying to shield Cas who was staying low to the ground as best as he could while shooting. Benny must have rolled somewhere else because he wasn't with them. There was swearing and yelling from both sides that was making the noise level overwhelming.

To add to the cacophony of sound, police sirens started to wail. Cas had never heard a more beautiful sound.

_Thank God they're here,_ Cas thought for once in his life about the cops.

"Dean, we're going to be okay," Cas said, so quiet he didn't even know if Dean heard him. But he needed to say it anyways, even if just for himself. "Dean?"

Cas got up into a kneeling position as they gunfire lessened and the sirens got louder. He could hear an abundance of footsteps as guys from both side headed to the nearest door.

"Fuck, Cas," Dean said. His eyes were closed.

"Dean, what's wrong?" Cas said, forgetting about the gang members, guns and police. Dean was holding his left shoulder and when he pulled it away, there was blood. A lot of blood. He'd been shot.

"DEAN!" Cas yelled. "Dean, stay with me, keep your eyes open, damn it!"

The cops had finally come in. Cas saw Henriksen first.

"Henriksen, call an ambulance, please," Cas begged. Despite their differences, Henriksen wasn't actually a bad person and immediately radioed for an ambulance. Mills rushed over to help apply pressure to Dean's shoulder. Dean's eyes fluttered open, meeting Cas's.

"Cas…"

"I'm here, you're going to be fine, Dean," Cas whispered. Dean had fallen back onto Cas's lap and his eyes closed again.


	38. Frenemy

**AN: You know me, love me some cliffhangers! Thank you for the reviews, I hope nobody panicked too much. Mostly. Enjoy!**

Paramedics rushed into the warehouse after the eternity it felt like it took them to get there. Henriksen quickly directed them from the front door to where Dean was lying unconscious on Castiel, still bleeding profusely. Cas didn't want to let go of Dean but he had to let them take him.

He followed the stretcher carrying Dean blindly out the door and towards the waiting ambulance. Cas was all set to get in and go with Dean to the hospital, had every intention of staying by Dean's side until he knew he was okay, but was stopped.

Mills put a hand on his shoulder. Cas tensed up. Did she really want to mess with him right now?

"Castiel, you have to come with us," she said, low so only he could hear it, "you can't blow your cover."

"I don't care, I'm going with Dean," Cas said in a low, dangerous voice. Just as dangerous was what he was willing to do in that moment to make sure he was with Dean, holding his hand.

"No, you're not," Henriksen stepped beside Cas. "You heard her, you can't…"

"Screw you! I don't care!" Cas yelled, not caring about his damn cover. Dean, _his_ Dean, was in an ambulance, had been _shot_ and these two were telling him he couldn't go with him?

He made a feeble attempt to run to the ambulance before it drove away. Henriksen grabbed him around the middle and Mills put both hands on his shoulders to push him back. Henriksen handcuffed him and half-dragged him to the squad car. He kept fighting them both until the ambulance doors closed and it started to drive away. He let out a breath and all of the fight left in him went with it.

That's when Cas began to cry. Cried for Dean, for himself, the shitty situation he had gotten himself into and the general _suck_ that had been his life. The suck that had existed until he had met Dean. And now he might be taken away from him, too.

Cas had been oblivious to anything besides Dean until that point and he now looked around through blurry, tearful eyes as he was loaded into the squad car. Crowley and Dick had been grabbed as well as a couple of guys from Michael's gang, Uriel and the blonde one with his usual black V-neck, or at least that's what Cas remembered him in from last time.

Crowley had an initial look of disbelief but then attempted to look expressionless. Hopefully, Mills was right and Crowley would continue to believe Castiel wasn't working with the police. It was generally impossible to tell what Crowley was thinking or scheming.

The ride, while short, was excruciating. They needed to hurry so Castiel could run to Dean at the hospital. Considering his lack of a car, that would probably be literal. The entire car ride for Cas was full of almost every memory he had of Dean. He tried to block them out and to just focus on what was happening now or to just stare out of the window but they surfaced anyways. The first time he met him, their fight in the diner, their first kiss on the Impala, their dates…

Cas never told him he loved him, told him _why_ he loved him. How he was with Sam, the soft side under his bad boy exterior, his passion for cars, the way he looked at Cas…

_What if you never get to?_ whispered the sinister part of Cas's brain. He squinted his eyes shut, hard, and tried to block that thought out as tears continued to stream down his face.

* * *

They got to the station and Castiel sat down in the interrogation room. It was cold and bare, which wasn't helping Cas's mood but nothing really would have at that point except to see Dean, healthy and smiling. He quickly wiped the tears from his face and tried to pull himself together to get out of there as soon as possible.

"We're sorry about what happened…"Henriksen started to say.

"No, you're not," Cas said, glaring at him. "I'm surprised you showed at all."

"I get you're mad…" Mills tried but Cas cut her off, too.

"You think?" he snapped, lashing out. He almost felt bad seeing the hurt cross her face because he never had a problem with her and still didn't, but he couldn't bring himself to care. "How'd you know we were there, anyways?"

"GPS on your phone," Henriksen answered like that was obvious. If Cas had been thinking clearly, it would have been. He also wasn't thinking clearly enough to find that invasion of privacy disturbing.

"We didn't get a chance to see the supplier. Did you get a name?" Mills asked, treading gently.

"Yes," Cas sighed, "Lucifer."

"Was that his real name or a street name?" Henriksen asked, almost smirking, which pissed Cas off.

"How the fuck would I know? Everyone started shooting before I could ask him," Cas retorted, shocking himself. Sure, he'd been upset and short with these two before but he never would have talked like that to a cop quite like that before meeting Dean. He looked down at his still handcuffed hands in his lap.

"Can I go now?" Cas asked quietly. He needed to get to Dean and he needed to go before he said something he's regret because he was upset.

Mills unlocked the handcuffs and let him go.

* * *

Outside the precinct, Cas smelled cigarette smoke and immediately thought of Dean. He turned to his left but, of course, he was disappointed. Instead of Dean, he saw the black V-neck wearing gang member from Michael's crew smoking and froze, anticipating a fight.

"Whoa, easy," the blond said, dramatically throwing his hands in the air, "I'm just glad to be out of there," he gestured with his head towards the station, "I don't want any trouble."

"Same," Cas agreed. He paused, looking left and right to try and pick which way was quickest to the hospital.

"What are you looking for, your guys aren't coming, right?" the guy asked, puffing his smoke. Cas shook his head. They weren't exactly Cas's guys anyway but this man didn't need to know that.

"Thinking of how to get to the hospital, not that it's any of your concern," Cas said.

"I was about to head over myself. One of your guys hit at the warehouse?" he asked, stomping out his cigarette. Cas nodded. "Need a lift?"

Cas figured it was a bad idea, a trap maybe, but that was the fastest way to Dean so he didn't care.

"Sure. Thanks," Cas said, feeling the tension in his face, shoulders and everywhere melt just a little.

"Balthazar," the man said, extending a hand. Cas rethought what he was about to do for a split second before deciding a course of action.

"Cas," Cas said, shaking it.


	39. Everyone Hates Hospitals

Castiel threw caution to the wind and got in the car with Balthazar. The risk was worth it if he could get to Dean, he reasoned, and he needed to get there _now._ Talking to the police already wasted too much time.

"So, Cas," Balthazar said casually as he drove, "Which one of your boys got shot?"

Cas's first response was disbelief. How could he be so cavalier about this situation?

"Dean," Cas said, glad he didn't start crying again. He realized Dean might not have been the only one that got hit. "At least, I think that he was the only one, he was the only one I was paying attention to."

Balthazar raised his eyebrows. "Dean, huh? Bummer."

"You don't sound like you think it was a bummer," Cas observed, wishing he would drive faster.

"Well…"

"Look, I get it, you don't like each other. But you don't have to be an ass."

"Hey, I'm driving you, aren't I?" Cas couldn't argue with that. They rode the rest of the way in silence.

* * *

The two arrived at the hospital. Once inside, the unlikely pair headed to the front desk of the emergency area.

"Can I help you?" the friendly nurse said.

"Yes, I'm looking for a patient, would have just come in with a gunshot wound, Dean Winchester?" Cas said in one breath.

"Are you family?" she asked with a smile.

"Uh," Cas paused but knew the answer to get in to see him, "Yeah, his…cousin."

The nurse looked a little skeptical but nodded and told him a room number. He left Balthazar after a hurried thanks for the ride and practically ran to Dean's room.

It was empty.

Cas stood in the doorway, dumbfounded.

"Are you looking for Mr. Winchester?" a tall doctor with shoulder length brown hair came up and asked. Cas couldn't help but notice the doctor was wearing cowboy boots.

"Yes, where is he?" Cas demanded, turning on the doctor who took a step back.

"Whoa, easy," the doctor said. "He just went up to surgery, the bullet hit an artery."

Cas let out a deep breath and closed his eyes.

"Is he going to be okay?" he asked with his eyes still closed.

"It's hard to tell," the doctor said, "the blood loss alone…"

Before Cas knew what he was doing, he grabbed the doctor by the shoulders and turned, slamming him into the wall.

"You _have_ to save him, that's your JOB!" Cas yelled. The doctor shoved him off and said nothing as he stormed off down the hallway. Cas leaned against the wall and slid down. There were no tears because he felt too empty. His head was resting on his knees.

_Shit_, he thought, head snapping up, _Sam doesn't know._ He had been too busy with the cops and worrying that he didn't even think.

Cas threw his head back, purposefully hitting the wall, hard. He pulled his phone out of his pocket. He was glad he saved Sam's number once when Dean was drinking, again, and he used his phone to call and tell Sam Dean was staying the night with him.

"Hello?" Sam answered.

"Sam, it's Cas."

"Cas, is everything…_Ruby, shut up,_ is everything okay?" Sam asked. Cas's stomach sank, knowing full well Ruby was bad for Sam. There was a more pressing issue at hand.

"Um, no…"

"Cas, what's wrong?" Sam said fearfully.

"Dean…got shot. I'm at the hospital now," Cas said, the pressure from holding tears in too much and a couple fell down his cheeks.

"Shit, really? Oh my God, okay. Okay, I'm coming. Thanks, Cas," Sam hung up before Cas could answer. It had sounded like he was running around, maybe grabbing his shoes. Castiel pulled himself up off the floor and moved to the waiting room where he ran into Balthazar again.

"How's Dean?" Balthazar asked, coming very close to genuine concern.

"In surgery. How's…who are you here for?" Cas asked, a little guilty he didn't ask before considering he was nice enough to drive him.

"Adam, he's new. I told Michael to stay out of the high school but he didn't listen," Balthazar said remorsefully. "Now, I'm the only one here. Surprise that I'm the nice guy."

They sat, both just waiting, in the gut-wrenching waiting room. It was sterile and depressing. It was empty besides the two of them or so Cas thought.

"Isn't this a sight," a voice drawled, sending a chill down Cas's spine. Cas turned to his left and found the source of the voice.

"Crowley, really not a good time," Cas snapped. "Why'd the police let you go?"

"I never actually did anything wrong, Lucifer made sure of that," Crowley said. "Why'd they let _you_ go?"

Cas stood up to face him. "Same reason."

"You finished telling them everything?"

"I didn't tell them anything," Castiel growled, "You should go."

Crowley seemed to ponder it then decided against making a scene in a hospital waiting room.

"Tell your boyfriend," Crowley paused and Cas tensed up, which caused Crowley to smirk, "I stopped by."

"Fuck," Cas said, sitting back down after Crowley left.

"Is he really your boyfriend?" Balthazar asked with a slight grin.

Cas just turned and gave him a look. Balthazar shrugged.

A doctor came through the doors leading to the rooms, a different one than Cas encountered earlier.

"Are either of you here with Adam Milligan?" she asked.

"Yeah, I am. What's the news, doc?" Balthazar answered.

"He, um… I'm afraid I have some bad news. Adam is dead," the doctor said with remorse.

"Damn it," Balthazar cursed, "Well, thanks for telling me, I guess."

The doctor nodded grimly and left through the doors she came in through.

"Well, I guess I'm done here," Balthazar said, "gotta go tell the guys. See ya around, Cas."

Cas nodded and Balthazar left. Cas thought it was a little odd that Balthazar seemed to not care very much that one of his gang members died but didn't think much of it before Sam showed up.

"Cas, what happened?"

"We were in a warehouse and they were shooting at us…"

"A warehouse? Who's they?" Sam asked, obviously confused.

"Sam…" Cas was going to say he couldn't really explain it when the doctor Cas talked to outside of Dean's empty room returned. He seemed wary of Cas and eyed him with caution.

"Are you both here for Dean?" the doctor asked, noticing Sam.

"Yeah, I'm his brother, is he okay?" Sam replied. "Please tell me he's okay."


	40. Doctor Sexy & Good News

"He's resting after his surgery, you can visit him after he wakes up," the doctor said before leaving.

"Oh, thank God," Sam said as he collapsed back into his chair in the waiting room.

Castiel let out a huge sigh of relief and sat down as well. He closed his eyes and kept thinking "_He's fine, everything's going to be fine…"_ At least, Dean was going to be. Everything else would have to wait.

"Cas, you have to tell me what happened," Sam said. He shifted his body to face Cas.

"I can't, Sam," Cas replied, also turning in his chair. It was hard to look Sam in the eye because he was using what Dean called his "puppy dog" eyes.

"Why the hell not? My brother just got shot, I think I deserve to know what's going on."

"I know it's hard right now but…"

"Don't talk to me like I'm a freaking child!" Sam interrupted, his voice getting louder. One of the nurses turned her head with a disapproving look.

"Dean's just looking out for you," Cas said, his voice somehow still calm.

"Yeah," Sam scoffed, "_he _thinks."

"He's protecting you," Cas defended and Sam scoffed again. "I'm serious, Sam. It's the same reason he told you to stay away from Ruby."

Sam had a look of mixed shock, hurt and anger.

"You…you have no right…" he sputtered, "It's none of your business who I hang out with! Dean's either."

"He…"

"Don't you think you might have a biased opinion, considering he's your boyfriend? Just stop talking, Cas."

Cas shut his mouth and they sat in a pretty uncomfortable silence. Figuring no news was good news right now, he didn't mind waiting out here until Dean woke up, but the tension was eating at him. How could Sam not see where they were coming from? Sam could stay in blissful ignorance, focus on school, date Jessica, to be a normal kid. Cas knew that was all that Dean wanted, was for Sam to be happy and normal. And if Dean was happy, Cas was happy so he wanted that, too.

* * *

After what felt like hours but the clock on the wall said was only a half hour, the longhaired doctor returned to let them know Dean had woken up.

Sam and Cas followed the doctor to Dean's room, his cowboy boots clacking on the white linoleum. There was a curtain blocking the other half of the room as Sam and Cas walked in. It didn't matter of someone was on the other side, it only mattered what was on this side.

Dean was laying in the hospital bed in one of those awful gowns, a mint green one. He had an IV drip in his arm and chords to a heart monitor disappearing under the garment. Some of the bandaging from the wound was visible and his left arm was in a sling.

"Cas," Dean said, his voice hoarse. He still seemed very groggy from the anesthesia.

Castiel sat next on the right side of Dean's hospital bed in the plastic chair and held his hand. "Hello, Dean."

"Is Sam… where's Sammy?" Dean asked, brow furrowed.

"I'm right here, Dean. How are you feeling?" Sam said, standing on the left side of the bed. Dean's eyes slowly found him.

"How the hell you think? I've been shot, bitch," Dean said, before starting to cough.

"Not an excuse to be a jerk," Sam said before getting Dean a cup of water. Dean let go of Cas's hand briefly to drink the water before lacing their fingers together again.

"Did you meet my doctor? I'm calling him Doctor Sexy," Dean smiled at Cas, kind of out of it and a little loopy. Cas just laughed and shook his head.

"Isn't this touching," a voice said at the door. Three pairs of eyes snapped to the room's entrance to find a couple of police officers there.

"Henriksen, what do you want?" Dean snapped. The slight slur from exhaustion took a little away from the usual bite in his tone. He really wasn't in the mood.

"I wanted to bring you flowers," Henriksen joked. Dean rolled his eyes.

"If you didn't hear, Adam Milligan is dead," Officer Mills said.

"I heard," Cas said at the same time that Dean and Sam said, "Who?"

"One of Michael's guys," Henriksen explained. "So now, this is becoming a full blown investigation. Where's your gun, Dean?"

"My what? I don't own a gun!" Dean responded, incredulous. Sam looked startled and looked like he wanted to say something really bad or ask a million questions.

"Don't play dumb. Your gun. We need to check it out," Henriksen said snidely.

"I don't have it," Dean said. Cas didn't see it in the room and assumed the hospital staff put it somewhere. Somewhere, he hoped, that was safe.

"All right, we'll let you rest. But we'll be back with a warrant," Mills said, leading Henriksen out of the room with a hand on his shoulder. Dean let out a deep breath and Cas squeezed his hand.

"Dean…" Sam began, "Do you have a gun? Who's Michael?"

"Aw, come on, Sammy, you heard the cop. Let me rest," Dean said, closing his eyes. Sam glared but decided Dean was right and left the room.

"Oh, good, he's gone," Dean said, peeking open one eye to check the room. He opened the other looked at Cas. Cas got out of the chair to lean over Dean and give him a gentle kiss. His lips were a little dry but otherwise unaffected by everything that had happened.

"Dean," Cas sighed against Dean's lips. "You should rest."

Dean pouted. Cas laughed and kissed him again, quickly.

"You're killing me," Dean groaned as Cas sat back down.

"Go to sleep," Cas said. Dean raised his eyebrows. "Please?"

"Love when you get all commanding," Dean said, closing his eyes with a smile on his lips. Cas squeezed his hand again before leaning over on the bed to fall asleep, too. Forget the cops and their investigation, all that mattered was that Dean was okay.


	41. Whiskey Troubles

Dean was released from the hospital two days later and when he was home, the healing process was fairly quick or at least Dean pretended it was. He stopped wearing the sling sooner than he should have as per Doctor Sexy's orders and always insisted he didn't need Cas or Sam's help, which was crap. So they both did little things to make it easier for him without him knowing.

Cas ran into Balthazar on the street not too long after, luckily without Dean who would shoot first and ask questions later, and asked how their gang was taking Adam's death.

"Went over like a ton of bricks," Balthazar had explained, "Those guys cared about him, or pretended to. Michael even seemed a little upset. The one who actually recruited him, Zachariah, couldn't care less but that's because he's a prick." The two parted ways after their brief discussion before either of them were spotted by any gang member of either side.

Crowley made sure to still receive their shipment from Lucifer despite the stunt he pulled. He just kept it a one on one meeting and had Dick and Edgar tail Michael long enough to make sure their gang wouldn't show. This allowed the boys to continue to sell like usual. In hopes of keeping Crowley away from Sam, Dean returned to selling when his gunshot wound healed. Crowley was decent enough to allow him a little time off.

It was late September and Benny was getting closer and closer to his wedding. He seemed ridiculously stressed, more so than Cas had ever seen him, and Dean and Cas allowed him to skip selling and still get a cut to try to help him. Because Crowley valued Dean more and wasn't worried about Benny's significant other being a snitch, it didn't matter to him that Benny would occasionally not be on their corner.

Shockingly, Mills and Henriksen had been maintaining radio silence since the warehouse firefight. They hadn't visited Dean about his gun, which he thankfully got back from the hospital nor did they mention who they believed killed Adam Milligan. Castiel had heard nothing from them either. It was like waiting for a scorpion to strike out and sting, you don't know when it will happen.

On the last Saturday in September, Dean and Cas returned to Dean's thankfully empty apartment after selling and going for drinks at the Roadhouse. Dean had more than he had in a while so Cas, having had only one beer, drove them home in the Impala.

After pressing Cas against the closed front door and kissing him, hard, Dean stopped and smiled teasingly at Cas.

"Fuck, why are you stopping?" Cas moaned, wanting Dean's hands on him again and the taste of whiskey from his mouth. Dean kept smiling and headed into the small kitchen area and returned with a full bottle of what Cas guessed was more whiskey. He opened it and took a long pull and Cas was mesmerized by his mouth as he did. Dean led Cas with his other hand to the couch.

"Cas," Dean pleaded as they both sat, "drink some."

"Dean, come on," Cas protested. Cas had still never been drunk with Dean and usually only had a few beers at most. He just didn't see the point. But Dean just looked at him with his beautiful eyes and freckles and full lips and…

_Shit._

"Fine," Cas agreed. He took the bottle with slightly more force than necessary and took a small shot. Since he had never taken a straight shot before, he coughed and sputtered after. Dean laughed, loudly.

"Shut up," Cas wheezed, trying to pull himself together. Dean took the bottle again and drank.

"Get at my level," Dean slurred jokingly, purposefully sounding more drunk than he was. It felt like a challenge and Cas obliged. He boldly took another shot and this one went down a lot more smoothly.

They continued to make out on the couch, Cas on top, and occasionally took a break to drink more. Cas was taking the lead, moving his hips against Dean and gently biting his lower lip. When half the bottle was gone, Cas decided he had enough.

"I think I'm starting to feel something," Cas hiccupped, making Dean laugh. He went to drink more but was crazy drunk and Cas put the bottle back on the coffee table and kissed Dean.

They were interrupted by Sam who stumbled through the front door. Cas jumped off of Dean and immediately regretted moving so fast so quick as it did his stomach no favors.

Dean stood up slowly to confront Sam.

"Wha… what the shit, Sam, Sammy, are you _hic_ drunk?" Dean mumbled, staggering where he stood. Cas stayed on the couch where he tried to control his stomach.

"The fuck, look who's… who's talking," Sam slurred as he shut the front door.

"Well, yeah, but I'm older. You, you can barely drive!" Dean argued. Sam rolled his eyes.

Dean paused and inhaled, deeply. Cas couldn't see his face but he guessed he was narrowing his eyes.

"I swear, if that's weed…"

"What's it _hic _to you? You smoke it too and, and you did when you were _hic_ my age," Sam paused to burp, "Hell, Dean, you fucking SELL it!"

Dean froze up.

"Fucking Ruby," Dean muttered under his breath.

"Screw you, she has… nothing to do _hic _with this," Sam argued.

"Right," Dean said. Cas could hear the eye roll. "I said she was bad news."

"And I said screw you," Sam spat back. He headed towards his bedroom. Dean grabbed his arm as he walked past and Sam pushed him off. Dean's balance was off from drinking and he fell, landing on his bad left shoulder.

"God damn it," Dean cursed. Sam stopped by his door and he seemed to be on the brink of apologizing. Cas, who had been silent, finally got into action. He got on his knees on the floor next to Dean.

"I'm fine, I'm fine," Dean said, allowing Cas to help him only in the slightest to get up. "Sam, we're not done!"

"Yes, we are," Sam shot back, opening his bedroom door.

"Sam, get the fuck back here," Dean ordered.

"YOU'RE NOT DAD!" Sam screamed before slamming the door.

It shook the whole apartment and made Cas's ears ring. Dean sat back on the couch, looking exhausted. Cas joined him. Dean reached for the bottle.

"Dean, I think…"

"Cas, please," Dean begged. Cas caved and without looking at Cas, Dean drank.

"Do you want to ta…"

"Not at all. I want to sleep," Dean answered. He set the bottle down.

Cas followed Dean into his bedroom. They changed into comfier clothes and climbed into bed.

For a change, Dean was the little spoon and curled into Cas and pressed his back to Cas's chest. Cas held him tight.

"I'm sorry you had to see that," Dean said slowly.

"It's okay," Cas said, "families fight."

"Nah me n' Sam," Dean slurred, his tiredness and intoxication making him hard to understand. Also, Cas was listening through an alcohol-sloshed brain. "We don't…didn't. Always a _hic_ team against…"

His voice trailed off but Cas was curious.

"Team…against what?" Cas asked.

"Everything," Dean said, "but our dad mostly."

Cas was going to answer but Dean continued.

"Can we sleep?"

Cas nodded against Dean's shoulder and neck.

"Thanks, Cas. For…being you," Dean stumbled.

"You're welcome, Dean," Cas said, smiling a little.

"I l…" Dean yawned. Cas waited.

"Lo…" Dean seemed to forget what he was trying to say. "You."

That was the last word before his breathing slowed and Cas felt his heartbeat slowing down. It was pretty sobering and Cas found it hard to sleep until the alcohol won and slowly dragged him down.

Any other night, he wouldn't have gotten any sleep because his drunk boyfriend seemed to try to say, "I love you."


	42. Slip Sliding Away

The next morning, Cas woke up with a headache and the warmth of Dean pressed to his front. He nuzzled his face into Dean's neck and ran a hand up his side.

"Cas," Dean mumbled into his pillow, "fff mo' min…"

"What?" Cas asked in his ear. Dean moved his head just a little to get his face out of his pillow.

"Five more minutes," Dean muttered, eyes still closed, "My head fucking hurts."

"I'm sorry but we both have work. Up."

Dean turned his head back to kiss Cas. It started short and sweet, but Cas quickly deepened the kiss and snuck his tongue into Dean's mouth.

"Good morning to you, too," Dean laughed when they stopped to breathe. "I think I found the cure to a hangover." He kissed Cas again.

The two got up and got dressed before brushing their teeth. Castiel brushed his teeth, thinking about what Dean almost said last night. He was drunk and almost asleep and probably didn't mean to say it or remember saying it. Considering he didn't bring it up this morning, although Cas didn't expect him to anyways, he must not remember. But the fact that any version of Dean was close to saying "I love you" made Cas very happy.

Cas headed to the kitchen and made coffee while Dean stood in front of Sam's door, poised to knock.

"Sam? I'm going to work," Dean called. He paused, shooting Cas a concerned look who shrugged.

"SAM!" Dean called again. He opened the door and looked in. "What the fuck… he's gone!"

"Look, don't worry, he probably just went to study or hang with Jessica or something," Cas reasoned, trying to make him feel better. It was what Cas hoped for Sam, anyways.

"It's my job to worry about that kid, especially if he's getting drunk and smoking weed," Dean pointed out, walking into the kitchen.

"Just have some coffee…"

"I don't want coffee," Dean snapped. Cas glared at him. Understandably, Dean was upset but he didn't have to take it out on Cas.

"I get that you…" Cas started.

"No, you _don't_ get it, Cas," Dean said, looking right at Cas. They were standing a foot apart, facing each other, slightly menacingly. "I have to look out for him, keep him safe. He's my little brother."

Cas didn't want Dean to snap at him again so he said nothing, just kept his mouth in a straight line.

"I need to find him," Dean said, sounding slightly defeated and looking down. "He's the only family I have."

Cas tried to not to feel hurt that Dean only felt close to Sam. Without Sam, he still had him, his boyfriend. Maybe it wasn't exactly family but it was something.

"I know," Cas said, then looked at the clock, glad for an excuse to go. He didn't want to say something he'd regret. "And we will but I have to go."

"Yeah," Dean said, still distracted, "I'll, uh, see you later then."

The awkward tension that filled the air was almost suffocating. Cas nodded at Dean and left.

* * *

Dean spent Sunday under the hoods of several cars, getting good and dirty until it was quitting time. When he got home, still no sign of Sam and Cas hadn't called or texted.

The next morning, Dean called the school's attendance office and the secretary let him know that Sam was there.

_Oh, good, Ruby didn't get him killed,_ Dean thought bitterly. When Sam still never showed up to their apartment, at least while Dean was there, Dean decided to go have a chat with Crowley.

Dean drove over to Crowley's house and knocked on the door. Thankfully, he was home.

"Dean," Crowley smirked, wearing only a black robe, "What can I do for you?"

"First, you can put on some real clothes," Dean retorted.

"Not happening," Crowley responded. "Next?"

"You can tell Ruby to lay off my brother," Dean demanded.

"I only told her to drag your brother in while you weren't selling. I wanted at least one Winchester paying the debt for that old drunk's garage."

"Watch it," Dean growled, ready to pull his gun or punch Crowley or both. No one insulted Bobby Singer in front of Dean. Crowley put his hands up in surrender.

"Anything Ruby is doing now is of her own accord. I only control the bitch to a point," Crowley finished and went back inside, not letting Dean get a word in before he shut the door.

Dean tried Sam's cell, again, and it still went straight to voicemail.

* * *

Tuesday finished with still no Sam. Dean sent a quick update to Cas and got only one word answers. Dean figured that was problematic and maybe he was mad but that was a conversation for another time. Dean could only worry about so much at a time.

Wednesday morning, Dean again the attendance office but this time, there was no Sam. The only place he could think of was Ruby's. He had been once, a while back, for a party and still knew where it was.

Dean drove there and marched right to the door of the shitty run-down house. It was close to the street, one story and what was probably once white in color. Cigarette butts and empty beer cans littered the lawn. The door opened and behind it stood what looked to be an older version of Ruby, if she kept drinking, smoking and maybe took up meth.

"Who the hell are you?" the woman spat, drinking a beer despite it being nine in the morning.

"Mom, it's fine, he's a friend," Ruby said, coming out of nowhere. Dean hid his scoff at her use of the word.

Her mom grumbled into her beer and walked away. Ruby stepped on the concrete slab of a front stoop with Dean, closing the door behind her and crossing her arms.

"Well?" Dean asked.

"Well what?" Ruby answered.

"Well, where's my brother? You're not hiding him in this shithole are you?"

"Hey, don't be an ass," Ruby said. Dean sighed. It was mean to say but he wasn't taking it back.

"Is he here or not?" Dean asked.

"Not," Ruby replied. "Now, go away."

Her rough goodbye was fair considering Dean insulted her house and he left.

* * *

Wednesday night was getting darker. Sam still hadn't come home and Cas was still snippy in his replies.

Dean was sitting on the couch, staring at his phone in his lap when the front door opened.

"Sam!" Dean exclaimed as his little brother came home. He stood up. "Where the hell have you been? I've been worried sick! I called the school, they said you didn't show today!"

"So?" Sam shrugged.

"Are you kidding me? You're the star student, on the fast track to Stanford. You're going to get out of here, Sammy!"

"Don't," Sam rolled his eyes.

"Don't what?" Dean asked.

"Don't lecture me about grades and college and shit, okay? I get it at school from the teachers who say I have 'so much potential' and I got it from Dad."

"But Sam, you have to be the Winchester that goes somewhere, man!"

"Why? Why does it have to be me? Just leave me alone, I want to go to bed."

Dean didn't know what to say so he let Sam pass without a word.

Since when did Sam change so much? Was it because of Ruby or was it before then? Had Dean been too caught up with Cas that he neglected his only brother?

Dean sat on the couch and picked up his phone.

**Dean: Sam's home**

**Cas: Glad to hear it.**

On top of the problem with Sam, what was going on with Cas? Everything was giving Dean a headache so he walked to the kitchen and grabbed the bottle of whiskey sitting there and went into his room. He drank until he wasn't thinking about Cas or Sam or anything at all.

**AN: I appreciate the reviews, thanks guys! Reminder, my tumblr is on my profile page if you want it.**


	43. Gone

Thursday morning was bright. Way too bright for Dean, who was unfortunately very hungover. He always hated himself the morning after drinking but he could always count on Sam to make him a nice, greasy breakfast.

_Fuck_, Dean thought, remembering that Sam had gone off the rails. His once caring and thoughtful brother was smoking weed and getting drunk with freaking Ruby. It might be hypocritical of Dean, who did that at sixteen too, but this was Sam and it was with Ruby. Sam was going places and Dean knew he never had the chance. He could pretend getting his GED with Cas made a difference but it was really for Cas. Cas was smart, like Sam, and had gotten screwed by a shitty situation. Both of them would get to college if Dean had anything to do with it.

Dean got up regretfully from his comfy bed and checked the apartment. No Sam. Making matters worse, his booze was now gone because of his own stupid, borderline alcoholism. He'd need to get more.

_Fuck_, Dean thought again. A few quick phone calls confirmed that Sam was not at school or with Ruby. Crowley had no idea either, but that wasn't a shock.

Dean went to Bobby, Ellen and Jo's apartment, which was one floor under theirs. None of them had seen him anywhere recently, not in the building, the garage or the Roadhouse. Dean was grasping at straws and in a last ditch attempt, drove to Jessica's house when school was out. He knew where it was from dropping Sam off before on his way to work.

"Hey, Jess," Dean greeted when she opened the door. When she saw him, she scowled. "No chance Sam's here, is there?"

"No chance in hell," Jess said angrily, "When you find his ass, tell him we're through!"

She slammed the door in Dean's stunned face.

* * *

_How far gone was Sam? _Dean thought, the pit in stomach getting heavier. _How did he manage to mess this up?_ Jess seemed great and Sam had somehow ruined what they had. Dean really needed to find him before anything else happened.

"Hello?" Cas answered his cell. Dean called him as a last hope. Everyone else was busy with work or school or a wedding leaving Dean to find his little brother, his one responsibility.

The number one of rule of protecting Sam had been pounded into his brain for so long he said stupid shit to the guy he, in all honesty, was probably in love with. If only John knew _that_…

Forget John, right now he needed Cas.

"Cas? Hey, man, it's me, I need your help," Dean said from the other line, nervous to Cas's reaction.

"Really," Cas replied drily. That was kind of what Dean expected.

"Look, I know I was an ass…"

"Understatement."

"But, seriously, I need your help," Dean pleaded. If Cas said no, there was no one else for Dean to turn to for help.

"Why _my_ help?" Cas asked, knowing the several people Dean could go to instead, his _family. _Cas was bitter, sure, and he wasn't going to sugarcoat that.

"Because you're the only one who will help me, okay?" Dean admitted. It felt kind of lonely to admit out loud.

"Fine," Cas sighed. "I'll come over." He hung up before Dean could say anything.

_This will be fun_, Dean scoffed to himself.

* * *

Cas showed up at Dean's apartment door with his arms crossed.

"Hello, Dean," Cas said, but it was cold, lacking the usual warmth when Cas said Dean's name. There were several different ways Cas said Dean's name but this was new and it chilled Dean.

"Uh, hey, Cas," Dean stammered, rubbing the back of his neck as he let Cas in and shut the door.

"So, I take it I'm here because Sam is missing again," Cas guessed.

"Yeah, he was here last night but he left. He was being all sullen and shit, too," Dean explained.

Cas eyed the empty whiskey bottle Dean had placed on the kitchen counter with raised eyebrows but didn't mention it. Picking a fight wouldn't help find Sam. They had talked about Dean's drinking before and Cas had changed the subject before it got to be a fight.

"Where have you looked so far?" Cas asked, figuring if he was here, he could be useful.

"Um, Crowley's, Ruby's, Jess's, the garage, the Roadhouse… he didn't go to school either," Dean listed.

"Is there any other possible place he would go?" Cas asked. The list Dean made felt pretty exhaustive but Cas didn't know Sam like Dean did. There had to be somewhere else.

"Maybe. Let me check his laptop in his room," Dean said. He headed into Sam's room and Dean followed. Not surprisingly, there was a periodic table of the elements on the wall and pre-law books already on his bookshelf in hopes of being a Stanford-educated lawyer. It was smaller than Dean's and Cas had a hard time picturing Sam and Dean sharing it before John died and Dean took his room. It would have been ridiculously tight.

Dean opened Sam's laptop and attempted to log onto it. The picture for the log on screen was one of Sam and Jess.

"You know his password?" Cas asked.

"No, but I can guess it," Dean said. Soon enough, he was in and checking the browser history. Dean made a joke about Sam being so clean and prude but Cas just rolled his eyes. Dean cleared his throat and kept looking. Besides links obviously used for homework, there was a recent one that held the answer.

There was purchase for a bus ticket from Chicago to Kansas City.

"Why Kansas City?" Cas asked, assuming that's where Sam ran off to but it seemed random.

"Because it's next to Lawrence," Dean explained. Cas remembered Dean saying it's where his parents were from but… "I was scared of this."

"Why?"

"Our grandparents still live there. He went to our grandparents," Dean sat back in his chair. He ran both of his hands fitfully through his hair.

"Oh," Cas said. He didn't even know Dean's grandparents were still alive let alone why it would it be such a bad thing Sam went there.

"Okay, this says it's an eight hour drive and it's already six so maybe stop somewhere a little over halfway…"

"Whoa, what?" Cas asked, taken aback. Dean was just going to up and drive to Kansas?

"Cas, I have to go get him," Dean said point blank.

"Couldn't you just call your grandparents?" Cas spit-balled. It seemed easier to get them to send Sam back then driving all the way to get him.

Dean just laughed a little and Cas figured Dean _really_ didn't want to talk to them.

"Are you coming?" Dean asked, looking Cas in the eye with fierce determination.

Cas took a deep breath and let it out with his obvious answer.

"Of course."


	44. On The Road

Dean and Cas got into the Impala after Dean quickly packed an overnight bag and they headed to Cas's apartment so he could grab some stuff for the impromptu trip.

"I'll be right back," Cas said as they pulled up in front of his building, "I'll have to leave a note for Gabriel."

Dean nodded but was looking out the window and drumming on the steering wheel with his thumbs, distracted.

When Cas came back down, they hit the road.

"So, are you going to tell me why you've been pissy all week?" Dean asked, not beating around the bush at all. He wanted to know what Cas's deal had been all week.

"You really don't know why?" Cas responded, a little shocked Dean was this oblivious.

"No, that's why I asked," Dean rolled his eyes then kept them on the road. Cas looked at him in disbelief and then shook his head.

"What?" Dean demanded, sparing a glance at Cas.

"It will be a long car ride if we argue," Cas said, trying to just drop it.

"Yeah, well it will be longer if we just ignore whatever's going on," Dean pointed out.

"Fine," Cas agreed.

"Fine," Dean said. "So, what's wrong?"

"You. _You _are what's wrong."

"_Me_? What did I do?" Dean snapped.

"When Sam went missing on Sunday, you could have asked for help, my help, but instead you'd rather deal with it yourself until you have no choice but to ask me. You think you have to carry the weight of everything on your own and you don't," Cas explained.

"You kind of just up and left on Sunday," Dean said, trying to defend himself.

"Well, you were kind of rude," Cas argued. Dean opened his mouth and then closed it, realizing he was right.

"So, this whole week…"

"I was basically waiting for you to finally ask for my help. I was there, Dean. I'm always there for you."

Dean didn't say anything but seemed a little more relaxed.

"Also, I've been in foster homes with younger boys I felt were like little brothers to me," Cas continued. "So, I do know what it's like to take care of them."

"Shit, Cas, I didn't know," Dean said, looking a little guilty.

"Well, I would have said it on Sunday if you hadn't been in such a bad mood," Cas explained.

"I'm sorry for being an asshole this week, Cas," Dean apologized. "I know you wanted to help and I should have been smart enough to come to you in the first place. I mean, that's what boyfriends are for, right? To help find missing little brothers?"

Cas laughed and so did Dean who took the laugh as a sign that they were okay.

Everything was pretty much okay. The continued to drive, stopping only once for a bathroom break and so Dean could have a quick cigarette. Cas had forgiven Dean for being too wrapped in his family drama to bother with Cas. He understood how much Dean loved and cared for Sam and was glad he came with.

When they were driving into Kansas City, where they planned to stay the night until moving onto Lawrence tomorrow, Dean brought up Benny's wedding that was in two days.

"I'm excited, I've never been a best man before. I didn't think I would be one until Sammy's wedding," Dean admitted.

"I've never been a groomsman. There aren't many people who would invite me to their wedding let alone want me in the wedding party," Cas said, understanding where Dean was coming from.

Castiel really only had Gabriel besides Dean and the idea of the wild Gabriel getting married was laughable so he wouldn't be in that wedding party anytime soon. And the thought of being a groomsmen and not the other _groom_ at Dean's wedding made Cas sick.

_Whoa_, Cas thought, _where did _that_ come from? _He hadn't thought about them like that before. It must have just been the closeness to a wedding, makes couples think about their own futures.

"Cas?" Dean said, snapping Cas out of it, "did you hear anything I said?

"I…no," Cas said honestly, still a little thrown off by his own head, "I'm sorry, I was distracted."

"It's fine, I was just thinking… well, at weddings," Dean said, clearly trying to spit something important out, "people usually have dates."

"Right," Cas stated. He hoped he knew where Dean was going with this but wanted to watch him squirm and actually say it.

"But, we don't really want people to know, um, about us so…"

"Dean, what are you saying?" Cas asked, not liking the ditch this conversation turned into.

"We shouldn't go together, Cas, I mean we'll be there together, but not _together_ together, you know?" Dean stammered.

"What?" Cas snarled, angry again even though they worked out their previous issues.

"You take Meg and I'll go with Andrea's friend, Lilith."

"I don't want to go with Meg. I want to go with you, my boyfriend."

"Look, I want to go with you too but…"

"So, do it."

"It's not that easy," Dean tried.

"Actually, Dean, I'm pretty sure it is."

"I can't explain…"

"Try," Cas demanded. Dean ran a hand through his hair, shot a nervous look at Cas, then white-knuckled the steering wheel and kept his eyes set focused on the road.

"You know I like you, a lot," Dean said, making Cas think he was off to a good start, "but the bad guys know it and the guys in our gang know it."

"So?" Cas said, "Forget them."

"I wish I could."

"I don't care about them, they don't scare me."

"Well, they scare me," Dean said, pausing to let Cas take that in. "Do you realize how easy it was for Crowley to manipulate me into selling again by having Ruby just hang out with Sam? What if they did something to you?"

"I wouldn't let them and neither would you."

Dean smiled a little. "I can't let anything happen to you."

"Like me getting mad and running away to Kansas?" Cas snapped. It was a low blow and Dean's mouth set hard in a straight line but Castiel was sick of Dean's macho, white knight savior act.

"I can take care of myself and pretty soon, Sam will be able to, too. When are you going to look out for yourself, Dean? When are you going to realize there are people who care about you and who don't want you sacrificing yourself?"

"I guess never."

"That's stupid," Cas said, brutally honest.

"I was raised with one job, protect Sam. It's who I am, I protect the people I care about."

"Well, who protects you?"

"No one, I take care of myself," Dean stated.

"And you don't see that as hypocritical?" Cas asked. Dean didn't answer.

They were silent as they drove up to the motel. Dean parked and walked to the office, not checking if Cas was following him.

Dean was already talking to the desk clerk when Cas caught up, with enough time to hear the guy say the only rooms available were just one queen bed.

"Perfect," Dean said sarcastically.


	45. You Shook Me All Nigh Long

**AN: Warning for smut. **

They carried their duffel bags into the motel room and threw them on the cream carpeted floor by the door. Cas stayed by the door while Dean stood closer to the one bed. It had a hideous green and brown comforter on top of it. There was a bathroom, an old TV and a night stand on either side of the bed and that was about it.

"You know, I can sleep on the floor if it's such a big deal," Castiel sassed, continuing their fight. Dean turned to face him, emerald eyes enraged and narrowed.

"Oh, don't be a drama queen," Dean shot back, taking a step forward.

"I'm not. I just figured if you can't handle our relationship being out in the open, I guess you're not mature enough to handle sharing one bed," Cas continued, with a step forward of his own.

"We've shared a bed enough times, you know I can," Dean retorted.

"Do you have any notion of how profoundly vexatious you can be?" Cas pointed out. He took another step forward and was in Dean's face. Well, mostly. Dean was about an inch taller.

"You realize simple words work too so I don't need a fucking dictionary? You use such huge ass words when you get worked up," Dean accused.

"I do not!" Cas said, his voice getting a little louder. There was slight truth to what Dean was saying but there was no way Cas would admit it.

"Yes, you do!" Dean yelled.

"Just because you didn't…" Cas trailed off.

"Finish that sentence, I fucking dare you," Dean growled. "Didn't what? Finish high school, go to some prep school? Work in a damn library? So, I have a limited vocabulary?"

"That's not what I was going to say," Cas lied.

"Look, why don't you just shut the hell up?" Dean demanded.

"Make me," Cas retorted.

His voice was low and rough and just what Dean liked. With a quick glance to Cas's lips and back up to his eyes, Dean kissed Cas, roughly. Castiel almost pushed him off but he wanted this, wanted Dean. He was pulling Cas back to the bed by his hips, slightly biting Cas's bottom lip, making Cas moan.

Dean turned them around and Cas kissed back just as hard as they fell back onto the bed, Dean on top. The mattress squeaked under them. Dean sat up above Cas as he straddled his hips to quickly rip off his shirt. He got rid of Cas's just as fast, running his hands up his stomach and chest, and started to bite and suck Cas's neck, making sure to leave harsh marks.

Cas grabbed the hair at the back of Dean's head and sharply moved him so he could kiss him again, working his tongue into his mouth. The fight and the lack of touch since Saturday fueled them, both of them hard and straining against their jeans. Forget how stupid the fights had been, they were worth it if this was the end result.

Dean worked his hips against Cas to get some friction, anything, down there and Cas moaned into Dean's mouth and moved his own hips up.

"Cas," Dean groaned against Cas's neck, sucking and biting over the same bruises he just made on Cas's neck. He cupped Cas over his jeans making Cas arch his back on the bed.

"Fuck, Dean," Cas breathed.

"I told you to shut up," Dean smirked, stopping his hips, hands and lips. Cas whimpered at the loss of Dean's touch and movement.

"And I told you to make me," Cas challenged, enough to further spark Dean's interest. Dean worked off their pants and boxers with desperation. He stopped to look at Cas, grabbing his wrists to pin them up by his head as he did so.

"Fuck… so beautiful, Cas," Dean said breathlessly, eyeing his boyfriend up and down. He moved his hips again, the lack of clothes making the friction between them more intense. A quick pause allowed Dean to grab the lube and condom from his bag before returning over Cas.

"Presumptuous much?" Cas asked, eyebrows raised. It seemed a little odd to bring those on a trip to retrieve your runaway brother.

"I know you can't resist me," Dean joked, "and shush."

He set the condom aside and squirted some lube on his hand, warming it by rubbing his hands together before taking both of their lengths in a hand and moving up and down.

Cas threw his head back with a loud groan that only made Dean move his hand quicker.

"Dean," Cas moaned, already close and Dean knew it.

"Not yet," Dean said. He wasn't done with Cas. He slowed his hand down before letting go completely.

"Well, that didn't mean stop," Cas complained. He was laying naked under Dean and wanted something, anything...

"Tell me what you want then," Dean said suggestively.

"I want you to fuck me," Cas breathed. They had done this plenty of times but that it made no less thrilling.

Dean smirked again, pleased with that answer before adding more lube to his hand and he began to work Cas open with one finger.

Their fight had reminded Cas of their situation and how they met because of Henriksen and Mills' plan and that if it worked, Dean would go to jail. Cas felt guilty and immediately tensed.

"What's wrong?" Dean asked, feeling Cas tense and afraid he hurt him. He stopped moving his finger inside Cas.

"Nothing," Cas lied, "keep going."

Dean tried to make sure Cas was comfortable, as always, but this time Cas wasn't honest. Dean added second and third fingers and then finally his dick before Cas was completely stretched and ready. The burn was mixed with pleasure from Dean's hand on his cock and Cas felt that it served him right, the discomfort and bit of pain as Dean's thrusts increased intensity, for the deceit and betrayal.

And when they finally came together, Dean inside Cas and Cas in between their stomachs and chests, it was the most intense orgasm he'd ever had and the hardest he ever came.

It was just another reason for Cas to hate himself.

**AN: Thanks for the support as always!**


	46. Lawrence

**AN: Enjoy a chapter that's a little longer and happy season 10!**

The two of them woke up tangled together, still naked. It was early, about eight, but Dean said they should get going to Lawrence. They took separate showers then got their stuff to leave.

They got into the Impala that was right outside of their motel room after Dean checked them out at the front office.

"So," Dean said as he started the car and looked at Cas, "are we cool?"

"Yes, Dean," Cas laughed. "After last night, I would say we are 'cool.'"

The couple did seem fine, making their usual banter and just talking for the final forty-five minute leg of their journey.

As the car turned onto a quaint suburban road lined with identical houses and matching trees, Cas couldn't help but laugh a little.

"What?" Dean asked, a slight smile pulling at the corners of his lips just from Cas's laugh. He'd missed it.

"Nothing, it's just so… not you. I can't imagine if your parents had stayed here and you were stuck growing up in suburbia."

Dean laughed at the ridiculous idea.

It was hard to think of him, Sam and their dad playing football on the lawn while his mom baked a pie but it wasn't impossible. Their dad wouldn't have been sad or paranoid and it would have been, most of all, safe. Dean parked in the driveway of his grandparents' two-story house thinking maybe it wouldn't have been so bad. Maybe it wouldn't be so bad to escape the gang and the city and come here where people didn't get shot and he didn't have to sell drugs. Maybe Cas would come with him.

Quickly shaking that last thought away, Dean and Cas got out of the car and walked up to the front door. Dean looked at Cas who gave him a reassuring nod and the strength to knock.

An older guy, Cas guessed Dean's grandfather, answered the door. He was mostly bald, just a little bit of silver hair above his ears, and gray scruff around the lower half of his face. His expression, if Castiel had to describe it, was a sour lemon look like everything displeased him.

"I thought I heard that old junker," he said, his eyes shooting to the Impala in his driveway. "Come on in, I guess."

Dean set his mouth in a hard line and tensed but followed his grandfather inside. Cas was surprised Dean didn't go off on the old man for insulting his baby but said nothing as he too went inside.

They went into the living room that was to the immediate left of the front door. After Dean's grandfather sat in an armchair, he motioned for them to sit as well.

"Samuel, where's my brother?" Dean asked as he sat on the couch. Cas joined him.

"Upstairs, sleeping. It's pretty early after all," Samuel said, checking his watch. It was about nine thirty in the morning. "You two must have had a long drive."

Samuel looked pointedly at Cas who Dean hadn't had the opportunity to introduce.

"Oh, right. Samuel, this is Cas, my boyfriend. Cas, this is gramps."

"So, you're fine with him knowing?" Cas hissed under his breath. Dean nudged him with his elbow.

"Boyfriend, huh? I could have guessed that from the…uh…" Samuel motioned on his own neck where Cas had bruises from Dean. Cas didn't bother trying to hide them now but did blush a little. He almost forgot about those but they were a good memory, adding more heat to his warm face.

"Chalk that up to city living," Samuel muttered distastefully.

"What the hell is that sup…" Dean started but was interrupted by a woman who entered the room.

"Dean!" she exclaimed. She walked up with open arms and Dean stood to give her a slightly awkward hug, or at least Dean's face conveyed that.

"Hi," he said.

"And who's this?" she asked, looking at Cas. He already like her more than Samuel.

"My boyfriend, Cas," Dean explained.

"Boyfriend? Well, come here," she opened her arms for another hug which Cas gave. "I'm Deanna."

"Nice to meet you," Cas said, noticing but not mentioning that Dean was obviously named after her. Deanna smiled warmly.

"All right, we're going to get Sam and go," Dean said, determined. Deanna's smile faltered.

"Yeah, like hell you are," Samuel said, "he told us what happened!"

"Did he tell you I'm his legal guardian?" Dean replied. Samuel didn't have a response to that. "So, yeah, he's coming with me."

Before either Samuel or Deanna could react, Dean was heading up the stairs to find his brother. Cas stayed in the living room with Dean's grandparents, figuring Dean needed to talk to Sam alone.

Dean found the room Sam was sleeping in, a small one, and gently woke him up. Sam jumped awake from under a big plaid blanket and was very clearly shocked to see Dean.

"Dean?" Sam asked, rubbing sleep out of his eyes and sitting up. "What…How'd you find me?"

"There's only so many places you could have gone and come on, it's me. I'm an awesome older brother," Dean grinned, sitting on the edge of the bed. Sam didn't return the smile.

"You realize when someone leaves home they don't want to be found right?"

"Sam…"

"Dean, you were acting like Dad and I freaked, okay?"

"Sam, I know. And I'm sorry," Dean apologized. It used to be being compared to his father was a compliment but hindsight is twenty-twenty and that wasn't the case anymore. "But you belong at home, with me. It's you and me against the world, remember?"

"Not anymore," Sam grumbled.

"What do you mean?" Dean asked.

"You have Cas," Sam said, sounding more tired than angry. Like he was giving up.

"Well, you have Jess," Dean countered.

"Probably not now," Sam sighed. Dean didn't have the heart to tell him what Jess told him, he wasn't going to kick him while he was down. "I messed up, Dean."

Sam looked up at Dean and looked more like a scared little kid than Dean had seen him look like in a long time, probably since their dad died.

"It'll be okay, Sammy," Dean reassured. "We can fix this. Why don't we head home? You can apologize to Jess and maybe the four of us can go on a double date, huh?"

"What about Ruby?" Sam asked in a small voice.

"Don't worry about her," Dean said, trying hard not to get irritated. She didn't matter right now.

"I fell behind in school, Dean," Sam said, looking down.

"And you'll get back on track! If anyone can, it's you," Dean reassured. Sam looked back up.

"You think so?"

"I know so," Dean smiled. They stood up off of the bed and Dean pulled his brother into a hug.

"Glad to have you back, Sam," Dean said when they stepped back. "Let's go home."

Downstairs, Dean and Sam's return alleviated the awkwardness surrounding the trio Dean left behind.

"We're leaving," Dean stated, leaving no room for debate.

"Wait a minute," Samuel said, standing up. He seemed to not pick up on Dean's tone or just ignored it.

"Look, thanks for looking out for me…" Sam started.

"But, you've done enough. We're outta here," Dean finished.

"Why don't you stay…" Deanna said.

"Stay? Here?" Dean laughed harshly. "After all we've been through, you think we need _your_ help?"

"Dean," Samuel said.

"Where were you when mom died? When dad died? I was seventeen and Sam was thirteen and our dad died on Christmas, Samuel, and we were on our own. Where were you then?" Dean said heatedly, years of anger flowing out. "You hated our dad, fine, but you left your own daughter's children, your flesh and blood, on their own."

"We can help…" Deanna tried.

"We don't need your help. Not anymore," Dean snapped. "Let's go."

Dean stormed out the door and Cas and Sam followed into the Impala.


End file.
